Herbicidal S-substituted 1,2,4,6-thiatriazines

ABSTRACT

Compounds of formula (I) in which Qi is an unsaturated five-membered optionally substituted or condensed heterocyclic ring and X is O, S, SO or SO2, and agronomically tolerated salts/N-oxides/isomers/enantiomers of these compounds are suitable as herbicides

The present invention relates to novel herbicidally active thiatriazine derivatives, processes for their preparaiton, compositions which comprise these compounds, and their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.

Thiatriazine compounds are described, for example in Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem. Soc. 1989, 111, 1180-1185, DD 113 006 and in WO 96/01814. Novel thiatriazine derivatives having herbicidal and growth-inhibiting properties have now been found.

The present invention thus relates to compounds of the formula I

in which

Q_(i) is the group

R₂ and R₃ independently of one another are hydrogen, C₁-C₆alkyl or C₁-C₆alkyl substituted by S(O)_(n)R₆, halogen, cyano, nitro, C₁-C₈alkoxy, C₃-C₆trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₃-C₈cycloalkyl, C₁-C₅alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C₁-C₆alkylamino, C₁-C₅alkylcarbonyl, C₂-C₁₂dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or —CONR₈R₉, or

R₂ and R₃ independently of one another are C₂-C₆alkenyl or C₂-C₆alkenyl substituted by halogen, cyano, nitro, C₁-C₈alkoxy, C₃-C₆trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₃-C₈cycloalkyl, C₂-C₅alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C₁-C₆alkylamino, C₂-C₅alkoxycarbonyl, C₂-C₂dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or —CONR₈R₉, or

R₂ and R₃ independently of one another are C₃-C₆alkynyl or C₃-C₆alkynyl substituted by halogen, cyano, nitro, C₁-C₈alkoxy, C₃-C₆trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₃-C₈cycloalkyl, C₁-C₅alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C₁-C₆alkylamino, C₁-C₅alkoxycarbonyl, C₂-C₁₂dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or —CONR₈R₉, or

R₂ and R₃ independently of one another are formyl, C₁-C₁₅alkylcarbonyl, C₂-C₁₅alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl, C₆-C₉cycloalkenylcarbonyl or C₃-C₈cycloalkyl-C₁-C₆alkylcarbonyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, hydroxyl, amino, C₁-C₆alkylamino, C₂-C₁₂dialkylamino, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₁-C₈alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₁-C₈alkylaminocarbonyl or C₂-C₁₂dialkylaminocarbonyl, or

R₂ and R₃ independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted by halogen, cyano, nitro, C₁-C₅alkyl, C₁-C₅alkoxy, C₁-C₅alkylcarbonyl, C₁-C₅alkylcarbonyloxy, C₁-C₆alkoxycarbonyl, aminocarbonyl, C₁-C₆alkylaminocarbonyl or C₂-C₁₁dialkylaminocarbonyl, or heterocyclylcarbonyl substituted by halogen, cyano, nitro, C₁-C₅alkyl, C₁-C₅alkoxy, C₁-C₅alkylcarbonyl, C₁-C₆alkoxycarbonyl, aminocarbonyl, C₁-C₆alkylamino or C₁-C₅alkylcarbonyloxy, or

R₂ and R₃ independently of one another are phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenyl-C₁-C₆alkylcarbonyl, biphenyl-C₁-C₆alkylcarbonyl, naphthyl-C₁-C₆alkylcarbonyl, phenyl-C₂-C₆alkenylcarbonyl, biphenyl-C₂-C₆alkenylcarbonyl, naphthyl-C₂-C₆alkenylcarbonyl, phenyl-C₃-C₆alkynylcarbonyl, biphenyl-C₃-C₆alkynylcarbonyl or naphthyl-C₃-C₆alkynylcarbonyl, it being possible for these substituents to be substituted by C₁-C₅alkyl, C₁-C₅alkoxy, C₁-C₅alkylthio, C₁-C₅halogenoalkyl, C₁-C₅alkylcarbonyl, halogen, cyano, amino, nitro, —COOR₇, C₁-C₈alkoxycarbonyl, hydroxyl, C₁-C₅alkylsulfinyl, C₁-C₅alkylsulfonyl, C₁-C₆alkylaminocarbonyl or C₂-C₁₂dialkylaminocarbonyl, or

R₂ and R₃ independently of one another are phenyl or naphthyl, it being possible for there substituents to be substituted by halogen, cyano, nitro, C₁-C₅alkyl, C₁-C₅alkoxy, C₁-C₅alkylthio, —COOH, —CONH₂, C₁-C₆alkylaminocarbonyl, C₂-C₁₀dialkylaminocarbonyl, C₁-C₅alkylcarbonyl or C₁-C₅alkoxycarbonyl, or

R₂ and R₃, together with the nitrogen atom to which they are bonded, form a heterocyclic ring, which can be substituted by C₁-C₅alkyl, C₁-C₅alkoxy, halogen, cyano or nitro, or

R₂ and R₃ independently of one another are amino, C₁-C₆alkylamino, C₂-C₈dialkylamino, phenylamino, naphthylamino, C₁-C₆alkylcarbonylamino, C₁-C₁₀alkoxycarbonylamino, hydroxyl, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, phenoxy, biphenyloxy or naphthoxy, X is oxygen or S(O)_(x), in which x is the number 0, 1 or 2, and

R₄ is C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈alkynyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₃-C₈cycloalkyl-C₁-C₄alkyl or C₁-C₄alkyl-C₃-C₈cycloalkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, ═O or —OR₅, or

R₄ is phenyl, biphenyl, naphthyl, heterocyclyl, C₁-C₄alkylphenyl, C₁-C₄alkylnaphthyl, phenyl-C₁-C₄alkyl or naphthyl-C₁-C₄alkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, amino, —COOH, hydroxyl, C₁-C₁₀alkyl, C₁-C₁₀alkyloxy, C₁-C₆alkylamino, di-C₂-C₈alkylamino, C₁-C₁₀alkylthio, C₁-C₁₀halogenoalkyl, C₁-C₁₀halogenoalkoxy, C₁-C₁₀halogenoalkylthio, C₂-C₁₀alkoxycarbonylalkoxy, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆alkyloxycarbonyl, C₁-C₆alkylcarbonyl, —CONH₂, formyl, C₁-C₇alkylaminocarbonyl, C₂-C₁₁dialkylaminocarbonyl, C₃-C₆trialkylsilyl, C₁-C₁₀alkylcarbonylamino, C₁-C₁₀alkylcarbonyloxy, phenoxy, halophenoxy, pyridyloxy or by pyridyloxy substituted by halogen, C₁-C₄alkyl, C₁-C₄alkoxy, cyano, nitro or amino, or two substituents adjacent to each other on the phenyl or naphthyl ring R₄ form a carbocyclic or heterocyclic ring, which can be substituted by halogen, cyano, nitro, amino, —COOH, oxo, C₁-C₁₀alkyl, C₁-C₁₀alkoxy, C₁-C₁₀alkylthio, C₁-C₁₀halogenoalkyl, hydroxyl, C₃-C₁₀alkoxycarbonylalkoxy, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₂-C₆alkyloxycarbonyl, C₂-C₆alkylcarbonyl, —CONH₂, formyl, C₂-C₇alkylaminocarbonyl, C₃-C₁₁dialkylaminocarbonyl, C₃-C₆trialkylsilyl, C₂-C₁₀alkylcarbonylamino, C₂-C₁₀alkylcarbonyloxy, phenoxy, pyridyloxy or by pyridyloxy substituted by halogen, C₁-C₄alkyl, C₁-C₄alkoxy, cyano, nitro or amino, R₅ is hydrogen, C₁-C₆alkyl, C₁-C₆halogenoalkyl, C₂-C₅alkoxyalkyl, C₁-C₆cyanoalkyl, phenyl, phenyl-C₁-C₄alkyl, formyl, C₂-C₇alkylcarbonyl, C₂-C₇alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, C₂-C₈dialkylaminocarbonyl, benzoyl, halogenobenzoyl, C₁-C₆alkylamino, C₂-C₈dialkylamino, —N═CH₂, —N═CH—C₁-C₄alkyl, —N═C(C₁-C₄alkyl)₂, tri(C₁-C₄alkyl)silyl, C₃-C₇cycloalkyl, C₂-C₇alkenyl, C₃-C₇alkynyl or heterocyclyl,

n is the number 0, 1 or 2,

R₆ is hydrogen or cyano, if n is the number 0, or

R₆ is C₁-C₅alkyl, C₂-C₅alkenyl, C₃-C₅alkynyl, C₁-C₆alkoxyalkyl, C₁-C₅halogenalkyl, C₁-C₅hydroxyalkyl, phenyl, phenyl-C₁-C₄alkyl, heterocyclyl, heterocyclyl-C₁-C₄alkyl or C₃-C₇cycloalkyl,

R₇ is hydrogen, C₁-C₁₂alkyl, C₁-C₁₂halogenoalkyl, C₁-C₆nitroalkyl, C₁-C₆cyanoalkyl, phenyl, C₂-C₁₀alkoxyalkyl, C₂-C₁₀alkylcarbonylalkyl, C₂-C₁₀alkoxycarbonylalkyl, heterocyclyl, C₃-C₇cycloalkyl, C₁-C₇halogenocycloalkyl, —N═CH₂, —N═CH—C₁-C₄alkyl, —N═C(C₁-C₄alkyl)₂ or C₂-C₆dialkylamino,

R₈ and R₉ independently of one another are hydrogen, phenyl, C₁-C₈alkyl, C₁-C₈halogenoalkyl, C₁-C₈alkoxy, phenoxy, C₂-C₇cyanoalkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₂-C₈alkoxyalkyl, C₁-C₆alkylamino or C₂-C₆dialkylamino, or

R₈ and R₉, together with the nitrogen atom to which they are bonded, form a three- to seven-membered heterocyclic radical, which can contain one or two further heteroatoms and can in turn be substituted by C₁₋₆ alkyl groups or halogen,

R₁₀ and R₁₁ independently of one another are hydrogen, phenyl, C₁-C₈alkyl, C₁-C₈haloalkyl, C₁-C₈alkoxy, phenoxy, C₂-C₇cyanoalkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₂-C₈alkoxyalkyl, C₁-C₆alkylamino, (C₁-C₆alkylamino)-carbonyl, C₂-C₆dialkylamino, (C₂-C₂-C₆dialkylamino)-carbonyl, formyl, (C₁-C₇alkyl)-carbonyl, (C₁-C₆alkoxy)-carbonyl, phenylcarbonyl, phenoxycarbonyl, benzyloxycarbonyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl, or

R₁₀ and R₁₁, together with the nitrogen atom to which they are bonded, form a three- to seven-membered heterocyclic radical, which can contain one or two further heteroatoms and can in turn be substituted by C₁₋₆ alkyl groups or halogen,

R₁₂ is C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkenyloxy, C₁-C₈alkynyloxy, C₁-C₈halogenoalkyl, phenyl, phenyloxy, phenyl-C₁-C₄alkyloxy, C₃-C₈alkoxycarbonylalkyloxy or C₃-C₈alkylcarbonylalkyloxy,

R₁₃ and R₁₄ independently of one another are hydrogen, C₁-C₆alkyl, C₂-C₆alkylcarbonyl or phenyl,

R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are C₁-C₁₀alkyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-C₁-C₄alkyl, C₁-C_(alkyl-C) ₃-C₆cycloalkyl, C₂-C₁₀alkenyl, C₃-C₆cycloalkyl-C₂-C₄alkenyl, C₂-C₆alkenyl-C₃-C₆cycloalkyl, C₂-C₁₀alkynyl, C₃-C₆cycloalkyl-C₂-C₄alkynyl, C₂-C₆alkynyl-C₃-C₆cycloalkyl, C₅-C₆cycloalkenyl, C₅-C₆cycloalkenyl-C₁-C₄alkyl, C₁-C₆alkyl-C₅-C₆cycloalkenyl, C₅-C₆cycloalkenyl-C₂-C₄alkenyl, C₂-C₆alkenyl-C₅-C₆cycloalkenyl, C₅-C₆cycloalkenyl-C₂-C₄alkynyl, C₂-C₆alkynyl-C₅-C₆cycloalkenyl, C₃-C₆cycloalkyl-C₃-C₆cycloalkyl, C₅-C₆cycloalkenyl-C₅-C₆cycloalkenyl, C₃-C₆cycloalkyl-C₅-C₆cycloalkenyl, C₅-C₆cycloalkenyl-C₃-C₆cycloalkyl, C₂-C₈alkynyl-C₂-C₈alkenyl, C₂-C₈alkenyl-C₂-C₈alkynyl, phenyl, phenyl-C₁-C₄alkyl, phenyl-C₂-C₄alkenyl, phenyl-C₂-C₄alkynyl, heterocyclyl, heterocyclyl-C₁-C₄alkyl, heterocyclyl-C₁-C₄alkenyl or heterocyclyl-C₁-C₄alkynyl, it being possible for these groups in turn to be substituted independently of one another by halogen, cyano, azido, nitro, —OR₅, oxo, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉, —NR₁₀R₁₁, ═NR₁₂ or ═N—NR₁₃R₁₄, or

R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are hydrogen, halogen, cyano, azido, nitro, —OR₅, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉, —NR₁₀R₁₁, tri(C₁-C₄-alkyl)-silyl, tri(C₁-C₄-alkyl)-stannyl, tri(C₁-C₄-alkyl)-silyl-C₁-C₄alkyl, tri(C₁-C₄alkyl)-stannyl-C₁-C₄-alkyl, tri(C₁-C₄-alkyl)-silyl-C₂-C₄alkenyl, tri(C₁-C₄alkyl)-stannyl-C₂-C₄alkenyl, tri(C₁-C₄-alkyl)-silyl-C₂-C₄alkynyl, tri(C₁-C₄alkyl)-stannyl-C₂-C₄alkynyl, —B(OH)₂ or —B(C₁-C₄alkoxy)₂, it being possible for in each case two adjacent substituents R₂₁, R₂₂, R₂₃ and R₂₄ to form a five- to eight-membered ring with the two ring atoms to which they are bonded, it being possible for this ring system to be aromatic or partly saturated, carbocyclic or heterocyclic and furthermore to be substituted by halogen, cyano, azido, nitro, —OR₅, ═O, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉, —NR₁₀R₁₁, ═NR₁₂ or ═N—NR₁₃R₁₄, and agronomically tolerated salts/N-oxides/isomers/enantiomers of these compounds.

The alkyl groups which occur in the substituent definitions can be straight-chain or branched and are, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl or eicosyl, and branched isomers thereof. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl groups mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

Suitable cycloalkyl substituents contain 3 to 8 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Corresponding cycloalkenyl substituents can be mono- or also polyunsaturated, for example cyclopentadienyl or cyclooctatetraenyl.

If alkyl, alkenyl or alkynyl occur as substituents on a cycloalkyl, cycloalkenyl, phenyl, biphenyl, naphthyl or heterocyclyl, these ring systems can also be polysubstituted by alkyl, alkenyl or alkynyl.

Halogen is as a rule fluorine, chlorine, bromine or iodine. The same also applies to halogen in combination with other definitions, such as halogenoalkyl or halogenophenyl.

Phenyl can be unsubstituted or substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, C₁-C₄halogenoalkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or —CONR₈R₉.

Carbocyclic radicals which are formed by two adjacent substituents R₂₁, R₂₂, R₂₃ and R₂₄ and the two ring atoms to which they are bonded are, for example, benzene, where the group Q_(i) can be, for example, indol-2-yl

or 1H-indazol-3-yl

or cyclohexene, where the group Q_(i) can be, for example, 4,5,6,7-tetrahydro-benzo[b]thien-2-yl

or cyclooctane, where the group Q_(i) can be, for example, 4,5,6,7,8,9-hexahydrocycloocta[c]isothiazol-3-yl

Heterocyclyl is to be understood as meaning ring systems which, in addition to carbon atoms, contain at least one heteroatom, such as nitrogen, oxygen and/or sulfur. They can be saturated or unsaturated. Such ring systems preferably contain 3 to 8 ring atoms. This also applies to those heterocyclic radicals which, in the case of groups such as —NR₁₀R₁₁, are formed by two substituents bonded to a nitrogen atom.

Heterocyclyl ring systems in the context of the present invention can also be substituted. Suitable substituents are, for example, C₁-C₄alkyl, C₁-C₄halogenoalkyl, C₁-C₄alkoxy, cyano, nitro or C₃-C₆cycloalkyl.

Heterocyclyl as a substituent of a group Q_(i) can be, for example, epoxidyl, dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl (for example:

oxazolidinyl, imidazolinyl, imidazolidinyl or dioxanyl.

Heterocyclic radicals which are formed by two adjacent substituents R₂₁, R₂₂, R₂₃ and R₂₄ and the two ring atoms to which they are bonded are, for example, pyridine, where the group Q_(i) can be, for example, thieno[3,2-b]pyridin-2-yl

or pyrimidine, where the group Q_(i) can be, for example, thieno[2,3-d]pyrimidin-6-yl

or dihydrothiophene, where the group Q_(i) can be, for example, thieno[2,3-c]isothiazol-3yl

or tetrahydrofuran, where the group Q_(i) can be, for example, 2,6-dihydro-4H-furo[3,4-c]pyrazol-3yl

or thiophene, where the group Q_(i) can be, for example, thieno[3,2-b]thiophen-2-yl

where these examples do not represent a restriction to the invention.

Heterocyclic radicals R₆ are preferably, inter alia, pyridyl, pyrimidinyl and triazinyl.

Preferred heterocyclic radicals R₇ are, for example, oxetanyl, pyridyl, thienyl and furyl.

R₈ and R₉ preferably form rings, such as piperidinyl, morpholinyl and pyrrolidinyl.

Preferred examples of heterocyclic radicals formed by R₁₀ and R₁₁ or R₂ and R₃ with the nitrogen atom to which the substituents are bonded are piperidinyl, morpholinyl, pyrrolidinyl, triazolyl, tetrazolyl and imidazolyl.

Heterocyclic radicals R₉ are preferably thienyl, furyl, pyridyl and oxetanyl.

Phenyl and naphthyl rings R₄ can be substituted by carbo or heterocyclic radicals which are formed by 2 substituents adjacent to one another on these phenyl or naphthyl rings. The carbocyclic radicals preferably contain 4 to 6 carbon atoms, such as cyclobutyl, cyclopentyl and cyclohexyl. Heterocyclic groups are, in particular, dioxolanyl and tetrahydrofuryl.

Heterocyclic radicals R₄ such as succinimidyl, pyridyl, thienyl or furyl, can contain fused-on carbocyclic radicals, such as phenyl or cyclohexenyl.

Heterocyclic radicals R₂ and R₃ are preferably pyridyl, pyrrolyl and pyrimidinyl.

Heterocyclic radicals formed from —NR₂R₃ include, for example, succinimidyl, imidazolyl and triazolyl, it being possible for such groups to contain fused-on carbocyclic radicals, such as phenyl or cyclohexene.

Heterocyclylcarbonyl R₂ or R₃ is, for example, pyridyl, pyrrolidinyl, triazolyl, thienyl, furyl or isoxazolyl.

In substituents such as —N═C(C₁-C₄alkyl)₂, the alkyl groups can be identical or different. They preferably have the same meaning. The same also applies to the alkyl groups in dialkylamino, dialkylaminocarbonyl, trialkylammonium and trialkylsilyl substituents.

Alkali metals and alkaline earth metals are, for example, lithium, sodium, potassium, magnesium, calcium or barium.

The invention also relates to the salts which the compounds of the formula I can form, in particular, with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.

The alkali metal and alkaline earth metal hydroxides as salt-forming agents include the hydroxides of lithium, sodium, potassium, magnesium or calcium, but in particular those of sodium or potassium.

Examples of amines which are suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary C₁-C₁₈alkylamines, C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-iso-propylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, di-butenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; and primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but in particular triethylamine, iso-propylamine and di-iso-propylamine.

The compounds of the formula I contain a centre of asymmetry in the sulfur atom of the thiatriazine ring. Racemates, which can be separated into the corresponding enantiomers by customary separation processes, are therefore formed during preparation of these compounds. If further centres of asymmetry are present in the substituents of the thiatriazine ring, the corresponding diastereoisomers can also be separated in the customary manner. The present invention also relates to such diastereoisomers and enantiomers.

In preferred compounds of the formula I, Q_(i) is the group Q₁, Q₂, Q₃, Q₄, Q₅, Q₇, Q₈, Q₁₁, Q₁₃, Q₁₆, Q₁₇, Q₁₈, Q₁₉, Q₂₀, Q₂₁, Q₃₀, Q₃₃, Q₃₆, Q₃₉ or Q₄₀.

Compounds of the formula I which are furthermore preferred are those in which R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are C₁-C₁₀alkyl, C₃-C₆cycloalkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₅-C₆cycloalkenyl, C₂-C₈alkynyl-C₂-C₈alkenyl or C₂-C₈alkynyl, phenyl, phenyl-C₁-C₄alkyl, phenyl-C₂-C₄alkenyl, phenyl-C₂-C₄alkynyl, heterocyclyl, heterocyclyl-C₁-C₄alkyl, heterocyclyl-C₂-C₄alkenyl or heterocyclyl-C₂-C₄alkynyl, it being possible for these groups in turn to be substituted indepently of one another by halogen, cyano, —OR₅, ═O, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉ or —NR₁₀R₁₁, or

R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are halogen, cyano, tri(C₁-C₄alkyl)-silyl, tri(C₁-C₄alkyl)-silyl-C₁-C₄alkyl, tri(C₁-C₄alkyl)-silyl-C₂-C₄alkenyl, tri(C₁-C₄alkyl)-silyl-C₂-C₄alkynyl, —OR₅, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉ or —NR₁₀R₁₁, it being possible for in each case two substituents

R₂₁, R₂₂, R₂₃ and R₂₄ which are adjacent to form a five- to six-membered ring with the two ring atoms to which they are bonded, it being possible for this ring system to be aromatic or partly saturated, carbocyclic or heterocyclic and optionally substituted by halogen, cyano, —OR₅, ═O, —S(O)_(n)R₆, —COOR₇, —CONR₈R₉ or —NR₁₀R₁₁,

R₅ is hydrogen, C₁-C₆alkyl, C₁-C₆halogenoalkyl, C₂-C₅alkoxyalkyl, phenyl, phenyl-C₁-C₄alkyl, C₂-C₇alkylcarbonyl, C₁-C₆alkylaminocarbonyl, C₂-C₈dialkylaminocarbonyl, tri(C₁-C₄alkyl)-silyl, C₂-C₇alkenyl or C₃-C₇alkynyl or heterocyclyl,

R₆ is hydrogen, if n is the number 0, or

R₆ is C₁-C₅alkyl, phenyl, phenyl-C₁-C₄alkyl or heterocyclyl,

R₇ is hydrogen, C₁-C₆alkyl, C₁-C₆halogenoalkyl, C₁-C₆cyanoalkyl, C₂-C₁₀alkoxycarbonylalkyl, heterocyclyl, C₃-C₆cycloalkyl or C₂-C₆dialkylamino,

R₈ and R₉ independently of one another are hydrogen or C₁-C₈alkyl, or

R₈ and R₉, together with the nitrogen atom to which they are bonded, form a three- to seven-membered heterocyclic radical, which can contain one or two further heteroatoms and can be substituted by C₁₋₆ alkyl groups,

R₁₀ and R₁₁ independently of one another are hydrogen, phenyl, C₁-C₈alkyl, C₃-C₇alkenyl, (C₁-C₆alkylamino)-carbonyl, (C₂-C₆dialkylamino)-carbonyl, (C₁-C₇alkyl)-carbonyl, (C₁-C₆alkoxy)-carbonyl or heterocyclylcarbonyl, or

R₁₀ and R₁₁, together with the nitrogen atom to which they are bonded, form a three to seven-membered heterocyclic radical, which can contain one or two further heteroatoms and can be substituted by C₁₋₆ alkyl groups.

A prominent group is formed by those compounds of the formula I in which

R₂ and R₃ independently of one another are hydrogen, C₁-C₆alkyl or C₁-C₆alkyl substituted by halogen, cyano, nitro, C₁-C₄alkoxy, C₃-C₆trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₃-C₈cycloalkyl, C₁-C₅alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C₁-C₆alkylamino, C₁-C₅alkoxycarbonyl, C₂-C₆dialkylamino or phenyl, it being possible for the phenyl ring to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or —CONR₈R₉, or

R₂ and R₃ independently of one another are C₂-C₆alkenyl or C₂-C₆alkenyl substituted by halogen, cyano, nitro, C₁-C₄alkoxy, C₃-C₆-trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₁-C₆alkylamino, C₂-C₅alkoxycarbonyl, C₂-C₆dialkylamino or phenyl, it being possible for the phenyl ring to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄-alkylsulfonyl or

—CONR₈R₉, or

R₂ and R₃ independently of one another are C₃-C₆alkynyl or C₃-C₆alkynyl substituted by halogen, cyano, nitro, C₁-C₈alkoxy, C₃-C₆trialkylsilyl, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₁-C₆alkylamino, C₂-C₅alkoxycarbonyl, C₂-C₆dialkylamino or phenyl, it being possible for the phenyl ring to be substituted by halogen, cyano, nitro, —OR₅, —NR₁₀R₁₁, C₁-C₄alkyl, formyl, C₁-C₄alkylcarbonyl, COOR₇, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl or

—CONR₈R₉, or

R₂ and R₃ independently of one another are formyl, C₁-C₈alkylcarbonyl, C₂-C₈alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl, C₆-C₉cycloalkenylcarbonyl or C₃-C₈cycloalkyl-C₁-C₆alkylcarbonyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, hydroxyl, amino, C₁-C₆alkylamino, C₂-C₇dialkylamino, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₂-C₈alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₁-C₈alkylaminocarbonyl or C₂-C₈dialkylaminocarbonyl, or

R₂ and R₃ independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted by halogen, cyano, nitro, C₁-C₅alkyl, C₁-C₅alkoxy, C₁-C₅alkylcarbonyl, C₁-C₅alkylcarbonyloxy, C₁-C₆alkoxycarbonyl, aminocarbonyl, C₁-C₆alkylaminocarbonyl or C₂-C₈dialkylaminocarbonyl, or heterocyclylcarbonyl substituted by halogen, cyano, nitro, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, aminocarbonyl, C₁-C₆alkylamino or C₁-C₅alkylcarbonyloxy, or

R₂ and R₃ independently of one another are phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenyl-C₁-C₆alkylcarbonyl, biphenyl-C₁-C₆alkylcarbonyl, naphthyl-C₁-C₆alkylcarbonyl, phenyl-C₂-C₆alkenylcarbonyl, biphenyl-C₂-C₆alkenylcarbonyl or naphthyl-C₂-C₆alkenylcarbonyl, it being possible for these substituents to be substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄alkylcarbonyl, halogen, cyano, amino, nitro, —COOR₇, C₁-C₅alkoxycarbonyl, hydroxyl, C₁-C₄alkylsulfonyl, C₁-C₅alkylaminocarbonyl or C₂-C₆dialkylaminocarbonyl, or

R₂ and R₃ independently of one another are phenyl or naphthyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, —COOH, —CONH₂, C₁-C₅alkylaminocarbonyl, C₂-C₇dialkylaminocarbonyl, C₁-C₄alkylcarbonyl or C₁-C₅alkoxycarbonyl, or

R₂ and R₃, together with the nitrogen atom to which they are bonded, form a heterocyclic ring, which can be substituted C₁-C₄alkyl, C₁-C₄alkoxy, halogen, cyano or nitro, or

R₂ and R₃ independently of one another are amino, C₁-C₄alkylamino, C₂-C₆dialkylamino, phenylamino, C₁-C₅alkylcarbonylamino, C₁-C₅alkoxycarbonylamino, hydroxyl, C₁-C₄alkoxy, C₁-C₅alkylcarbonyloxy or phenoxy,

R₅ is hydrogen, C₁-C₆alkyl, C₁-C₆halogenoalkyl, C₂-C₆alkoxyalkyl, C₁-C₆cyanoalkyl, phenyl, halogenophenyl, C₁-C₄alkoxyphenyl, phenyl-C₁-C₄alkyl, C₁-C₄alkylcarbonyl, benzoyl, halogenobenzoyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₆trialkylsilyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl or C₃-C₄alkynyl,

R₇ is hydrogen, C₁-C₄alkyl, C₁-C₄halogenoalkyl, C₁-C₄cyanoalkyl, phenyl, halogenophenyl, C₂-C₄alkoxyalkyl, heterocyclyl or halogenoheterocyclyl,

R₈ and R₉ independently of one another are hydrogen, phenyl, halogenophenyl, C₁-C₄alkyl, C₁-C₄halogenoalkyl, C₁-C₄cyanoalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl or C₂-C₄alkoxyalkyl, or R₈ and R₉, together with the nitrogen atom to which they are bonded, form a heterocyclic radical, which can be substituted by C₁-C₄alkyl,

R₁₀ and R₁₁ independently of one another are hydrogen, phenyl, halogenophenyl, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄cyanoalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, C₂-C₄alkoxyalkyl, formyl, C₁-C₄alkylcarbonyl or phenylcarbonyl, it being possible for the phenyl moiety therein to be substituted by C₁-C₄alkyl, halogen, C₁-C₄alkoxy, hydroxyl, cyano, nitro or C₁-C₄alkoxycarbonyl, or R₁₀ and R₁₁, together with the nitrogen atom to which they are bonded, form a heterocyclic radical, which can be substituted by C₁-C₄alkyl.

Compounds of the formula I which are of particular interest are furthermore those in which

R₂ and R₃ independently of one another are hydrogen, C₁-C₆alkyl or C₁-C₆alkyl substituted by halogen, hydroxyl, amino, ammonium, tri-C₁-C₄alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C₁-C₅alkylcarbonyloxy, phenylcarbonyloxy, C₁-C₆alkylamino, C₁-C₅alkoxycarbonyl or C₂-C₆dialkylamino, or

R₂ and R₃ independently of one another are formyl, C₁-C₈alkylcarbonyl, C₂-C₈alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl, C₆-C₉cycloalkenylcarbonyl or C₃-C₈cycloalkyl-C₁-C₆alkylcarbonyl, it being possible for these substituents to be substituted by halogen, cyano, hydroxyl, amino, —COOH or —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, or

R₂ and R₃ independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted by halogen, cyano, nitro, C₁-C₅alkyl, C₁-C₅alkoxy or C₁-C₆alkoxycarbonyl, or heterocyclylcarbonyl substituted by halogen, cyano, nitro, C₁-C₄alkyl, C₁-C₄alkoxy or C₁-C₄alkoxycarbonyl, or

R₂ and R₃ independently of one another are phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenyl-C₁-C₆alkylcarbonyl, biphenyl-C₁-C₆alkylcarbonyl, naphthyl-C₁-C₆alkylcarbonyl, phenyl-C₂-C₆alkenylcarbonyl, biphenyl-C₂-C₆alkenylcarbonyl or naphthyl-C₂-C₆alkenylcarbonyl, it being possible for these substituents to be substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄alkylcarbonyl, halogen, cyano, amino, nitro, —COOH, C₁-C₅alkoxycarbonyl, hydroxyl or C₁-C₄alkylsulfonyl, or

R₂ and R₃ independently of one another are phenyl or naphthyl, it being possible for these substitutents to be substituted by halogen, cyano, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, —COOH or C₁-C₆alkoxycarbonyl, or

R₂ and R₃, together with the nitrogen atom to which they are bonded, form a heterocyclic ring, which can be substituted by C₁-C₄alkyl, C₁-C₄alkoxy, halogen or cyano and in which, in particular, R₂ and R₃ are hydrogen, or

R₂ and R₃ independently of one another are formyl, C₁-C₈alkylcarbonyl, C₂-C₈alkenylcarbonyl, C₄-C₉cycloalkylcarbonyl, C₆-C₉cycloalkenylcarbonyl or C₃-C₈cycloalkyl-C₁-C₆alkylcarbonyl, it being possible for these substituents to be substituted by halogen, cyano, hydroxyl or amino, or

R₂ and R₃ are phenylcarbonyl, it being possible for the phenyl ring to be substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, halogen, cyano, nitro, —COOH, C₁-C₅alkoxycarbonyl, hydroxyl or C₁-C₄alkylsulfonyl.

Another preferred sub-group is formed by those compounds of the formula I in which X is oxygen or S(O)_(x), in which x is the number 0, 1 or 2, and

R₄ is methyl substituted by halogen, cyano, nitro or OR₅, or

R₄ is C₂-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₃-C₈cycloalkyl-C₁-C₄alkyl or C₁-C₄alkyl-C₃-C₈cycloalkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, ═O or —OR₅, or

R₄ is phenyl substituted by halogen, cyano, nitro, amino, —COOH, hydroxyl, C₁-C₄alkyl, C₁-C₄alkyloxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄halogenoalkoxy, C₁-C₄halogenalkylthio, C₂-C₆alkoxycarbonylalkoxy, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₆alkyloxycarbonyl, C₁-C₆alkylcarbonyl, —CONH₂, formyl, C₁-C₅alkylaminocarbonyl, C₂-C₇dialkylaminocarbonyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₆trialkylsilyl, C₁-C₆alkylcarbonylamino, C₁-C₆alkylcarbonyloxy, phenoxy, halogenophenoxy or pyridyloxy, or

R₄ is biphenyl, naphthyl, heterocyclyl, C₁-C₄alkylphenyl, C₁-C₄alkylnaphthyl, phenyl-C₁-C₄alkyl or naphthyl-C₁-C₄alkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, amino, —COOH, hydroxyl, C₁-C₄alkyl, C₁-C₄alkyloxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄halogenoalkoxy, C₁-C₄halogenoalkylthio, C₂-C₆alkoxycarbonylalkoxy, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₆alkyloxycarbonyl, C₁-C₆alkylcarbonyl, —CONH₂, formyl, C₁-C₅alkylaminocarbonyl, C₂-C₇dialkylaminocarbonyl, C₃-C₆trialkylsilyl, C₁-C₆alkylcarbonylamino, C₁-C₆alkylcarbonyloxy, phenoxy, halogenophenoxy or pyridyloxy, and

R₅ is hydrogen, C₁-C₆alkyl, C₁-C₆halogenoalkyl, C₂-C₆alkoxyalkyl, C₁-C₆cyanoalkyl, phenyl, halogenophenyl, C₁-C₄alkoxyphenyl, phenyl-C₁-C₄alkyl, C₁-C₄alkylcarbonyl, benzoyl, halogenobenzoyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₆trialkylsilyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl or C₃-C₄alkynyl.

Preferred compounds from this group are those in which X is oxygen or sulfur and

R₄ is methyl substituted by halogen or cyano, or

R₄ is C₂-C₈alkyl, C₂-C₈alkenyl, C₃-C₈alkynyl, C₃-C₈cycloalkyl, C₅-C₈cycloalkenyl, C₃-C₈cycloalkyl-C₁-C₄alkyl or C₁-C₄alkyl-C₃-C₈cycloalkyl, it being possible for these substituents in turn to be substituted by halogen or cyano, or

R₄ is phenyl substituted by halogen, cyano, nitro, amino, C₁-C₄alkyl, C₁-C₄alkyloxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄halogenoalkoxy, C₂-C₆alkoxycarbonylalkoxy, C₁-C₄alkylsulfonyl, C₁-C₆alkyloxycarbonyl, C₁-C₆alkylcarbonyl, formyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₆trialkylsilyl or C₂-C₆alkylcarbonyloxy, or

R₄ is biphenyl, naphthyl, heterocyclyl, C₁-C₄alkylphenyl, C₁-C₄alkylnaphthyl, phenyl-C₁-C₄alkyl or naphthyl-C₁-C₄alkyl, it being possible for these substituents in turn to be substituted by halogen, cyano, nitro, amino, C₁-C₄alkyl, C₁-C₄alkyloxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, C₁-C₄halogenoalkoxy, C₂-C₆alkoxycarbonylalkoxy, C₁-C₄alkylsulfonyl, C₁-C₆alkyloxycarbonyl, C₁-C₆alkylcarbonyl, C₃-C₆trialkylsilyl or C₁-C₆alkylcarbonyloxy, in particular compounds of the formula I in which X is oxygen and

R₄ is phenyl or pyridyl substituted by halogen, cyano, nitro, amino, C₁-C₄alkyl, C₁-C₄alkyloxy, C₁-C₄alkylthio, C₁-C₄halogenoalkyl, halogenomethoxy, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino or C₂-C₆dialkylamino.

Compounds of the formula I which have particular importance are those in which

Q_(i) is Q₁, Q₂, Q₃, Q₄, Q₅, Q₇, Q₈, Q₁₁, Q₁₃, Q₁₇, Q₁₈, Q₂₀ or Q₃₃ and

R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are C₁-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₁-C₄alkoxy, fluorine, chlorine, bromine, phenyl, C₁-C₄alkoxy-C₁-C₄alkoxy, trimethlysilyl, trimethylsilyl-C₁-C₄alkyl, trimethylsilyl-C₂-C₄alkynyl, di-C₁-C₄alkylamino, di-C₁-C₄alkylamino-C₁-C₄alkyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxy-C₁-C₄alkyl, trifluoromethyl, hydroxy, phenoxy, phenoxycarbonyl or C₃-C₆cycloalkyl, it being possible for in each case two substituents R₂₁, R₂₂, R₂₃ and R₂₄ which are adjacent to form a five- to six-membered ring with the two ring atoms to which they are bonded,

R₂ is hydrogen,

R₃ is hydrogen or methylcarbonyl,

X is oxygen or sulfur and

R₄ is phenyl, naphthyl, pyridyl, or thienyl, or phenyl, naphthyl, pyridyl or thienyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy, fluorine, chlorine, nitro, cyano, C₃-C₆cycloalkyloxycarbonyl, C₁-C₆alkylthio, C₁-C₄hydroxycarbonyl, alkylsulfonyl, di-C₁-C₄alkylamino, C₁-C₄alkylsulfonyl or trifluoromethyl.

Compounds of the formula I which are of prominent importance are those in which R₂ and R₃ are hydrogen and Q_(i) is Q₂, Q₄, Q₁₇, Q₁₈ or Q₂₀.

The compounds of the formula I can be prepared in various ways via process steps which are known per se using known starting materials.

Compounds of the formula I can be prepared, for example, by reacting a trihalogenated thiatriazine of the formula II

in which the Hal independently of one another are fluorine, bromine or, in particular, chlorine, with the corresponding organometallic compound, to introduce the heteroaryl ring Q₁, of the formula III

Q_(i)—M  (III),

in which Q_(i) is as defined above and M is a mono- or polyvalent metal atom which can carry a number of Q_(i) groups depending on the valency.

Compounds of the formula II and their preparation are described, for example, in Chem. Ber. (1991) 124 1347-1352 and Z. Chem. (1976) 16 358-359.

Examples of suitable metals M are, in particular, lithium, magnesium, zinc, aluminium, silicon and tin, and furthermore also manganese, mercury and titanium. In addition to one or more Q_(i) groups, the polyvalent metal atoms can also carry further substituents, such as halogen, cyano, C₁-C₄alkyl, acetate, tetrafluoroborate or halogenated or non-halogenated alkanesulfonates. The organometallic compound of the formula IlI can furthermore be used in combination with salts, such as aluminium chloride, zinc chloride, tin chloride or cerium chloride or aluminium bromide and/or copper bromide, aluminium chloride and bromide and zinc chloride being preferred.

The compounds of the formula III can be prepared by customary methods, for example

by reaction of the corresponding halide Q_(i)-halogen with the metal M,

by a halogen-metal exchange reaction of the corresponding halide Q_(i)-halogen, in which halogen is preferably bromine or iodine, with a reactive organometallic compound, such as an alkyllithium compound, for example n-butyl- , s-butyl- or t-butyllithium,

by treatment of the corresponding heteroaromatic Q_(i)—H with a strongly basic compound, for example lithium diisopropylamide, lithium bistrimethylsilylamide, lithium tetramethylpiperidide, n-butyl- s-butyl- or t-butyllithium and the like. Heteroaromatics of the formula Q_(i)—H can also carry functional groups which facilitate the deprotonation and/or influence the orientation (cf., for example, Snieckus V. Chem. Rev. (1990) 90, 879-933, or Derek J. Chadwick et al. J. Chem. Soc. Perkin I Trans. (1977) 887-893, or Benjamin A. Anderson et al. Synthesis (1996) 583-585),

by a transmetallization reaction of an organometallic compound produced as described above with a derivative of another metal, for example a trialkylsilyl or trialkylstannyl halide (cf., for example, H. Zimmer et al. J. Org. Chem. (1984) 49, 5250-5253),

by treatment of the corresponding heteroaromatic Q_(i)—H with a metal salt, for example mercury halide or acetate.

Compounds of the formula III and solutions thereof are known and are in some cases commercially obtainable. As a rule, the organometallic compound is not isolated, but is reacted directly with the thiatriazine halide, if appropriate in the presence of a metal salt. Compounds of the formula Q_(i)—H and Q_(i)-halogen are known or can be prepared analogously to known methods (cf., for example, Comprehensive Heterocyclic Chemistry: The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds, Alan R. Katritzky and Charles W. Rees, (Editor: Kevin T. Potts), Pergamon Press, (1984), volume 4-6 and the literature references contained therein).

The introduction of the group Q_(i) can be carried out in an aprotic solvent, such as a hydrocarbon, for example hexane, heptane or toluene, or an ether, such as dioxane, diethyl ether or, in particular, tetrahydrofuran, at temperatures of (depending on the solvent) −100° C., to 150° C., in particular −80° C. to 50° C.

The introduction of the group Q_(i) can also be carried out by a Friedel-Crafts reaction between the heteroaromatic Q_(i)—H and a compound of the formula II, in the presence or absence of a catalyst, for example a Lewis acid (for example AlCl₃, SnCl₄, and the like) or activated clay (for examplel montmorillonite). This reaction can be carried out in an aprotic solvent, such as a hydrocarbon, for example nitrobenzene, benzene, carbon tetrachloride and the like, or an ether, for example, diethyl ether or tetrahydrofuran, at temperatures of (depending on the solvent) −50° C. to 120° C., in particular −10° C. to 60° C.

The resulting compounds of the formula IV

are novel and the present invention also relates to them.

The —NR₂R₃— and —XR₄ substituents can be introduced into the compound of the formula IV in any sequence.

The reaction of the compounds of the formula IV with the compoounds of the formula V

H—XR₄  (V),

in which X and R₄ are as defined above, to give the compounds of the formula VI

is advantageously carried out by a procedure in which, before the reaction with the compounds of the formula IV, the compounds of the formula V are pretreated with a base, such as a metal hydride, for example lithium, sodium or potassium hydride, a metal hydroxide, such as sodium or potassium hydroxide, or a basic salt, such as sodium or potassium carbonate, preferably in equivalent amounts. Alternatively, the reaction mixture of the compounds of the formulae IV and V can be treated with the bases mentioned. Suitable solvents for this step are hydrocarbons, such as hexane or toluene, halogenated hydrocarbons, such as chlorobenzene, ethers, such as tetrahydrofuran, dioxane or diethyl ether, and tertiary amides, such as dimethylformamide. It is also possible to employ a mixture of these solvents with water, a phase transfer catalyst then advantageously being used. The reaction temperatures are as a rule between −50° C. and 100° C., preferably between 0° C. and 40° C.

The compounds of the formula V are known and can be prepared in a manner familiar to the expert.

The compounds of the formula VI are novel and the present invention also relates to them.

The compounds of the formula VI can be converted into the end products of the formula I by reaction with a compound of the formula VII

 M₁—NR₂R₃  (VII),

in which R₂ and R₃ are as defined above and M₁ is hydrogen or a metal atom, such as lithium, sodium, potassium or calcium, the reaction advantageously being carried out in the presence of a base. Preferably, M₁ is hydrogen if R₂ and/or R₃ are hydrogen. If R₂ or R₃ is an acyl group, M₁ is preferably lithium, sodium or potassium.

Suitable solvents for this reaction are hydrocarbons, such as hexane or toluene, halogenated hydrocarbons, such as chlorobenzene or dichloromethane, ethers, such as diethyl ether, dioxane or tetrahydrofuran, alcohols, such as ethanol or isopropanol, esters, such as ethyl acetate, nitriles, such as acetonitrile, or water. The reaction temperatures are in the range from −70° C. to 100° C., in particular 0° C. to 40° C.

If M₁ is hydrogen, an acid-binding agent is preferably used in order to collect the Hal acid. This can be, for example, a second equivalent of the compound of the formula VII or a tertiary amine, such as triethylamine or pyridine, or an inorganic base, such as sodium carbonate or potassium carbonate or sodium bicarbonate. If R₂, R₃ and M₁ are hydrogen, an excess of base can be used. If appropriate, the reaction can be carried out under pressure.

The compounds of the formula VII and their preparation are described in the literature.

The reaction conditions to be maintained for the reaction of compound VI with compound VII are also to be observed if the compound of the formula IV is first to be reacted with the base of the formula VII. The compounds obtained in this manner, of the formula VIII

are likewise novel and the present invention relates to them.

The further reaction of the compounds of the formula (VIII) with the compounds of the formula (V) is carried out analogously to the procedure for the reaction of the compounds of the formulae (IV) and (V). In addition, however, a catalytic or, if desired, excess amount of an amine, such as trimethylamine, is added to the reaction mixture.

The end products of the formula I can be isolated in the customary manner by concentration and/or evaporation of the solvent and can be purified by recrystallization or trituration of the solid residue in solvents in which they do not readily dissolve, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, or by chromatographic methods.

Other compounds of the formula I can be prepared by customary derivatization of compounds of the formula I. The same applies to the intermediate products of the formulae IV, VI and VIII; for example by cross-coupling, ipso-desilylation or ipso-destannylation on the heteroaryl or derivatization on other parts of the molecule.

The compounds of the formula I according to the invention or compositions comprising these can be used in all the application methods customary in agriculture, for example preemergence application, postemergence application and seed dressing, as well as various methods and techniques, for example controlled release of the active substance. For this, the active substance is applied in solution to mineral granule carriers or polymerized granules (urea/formaldehyde) and the granules are dried. If appropriate, a coating which allows the active substance to be released in metered form over a certain period of time can additionally be applied (coated granules).

The compounds of the formula I can be employed in unchanged form, i.e. as they are obtained in the synthesis, but they are preferably processed in the customary manner with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. The methods of application, such as spraying, atomizing, dusting, wetting, scattering or pouring, like the nature of the composition, are chosen according to the desired aims and the given conditions.

The formulations, i.e. the compositions, formulations or mixtures comprising the active substance of the formula I or at least one active substance of the formula I and as a rule one or more solid or liquid formulation auxiliaries, are prepared in a known manner, for example by intimate mixing and/or grinding of the active substances with the formulation auxiliaries, for example solvents or solid carriers. Surface-active compounds (surfactants) can furthermore additionally be used in the preparation of the formulations.

Possible solvents are: aromatic hydrocarbons, preferably fractions C₈ to C₁₂, for example xylene mixtures or substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols, and ethers and esters thereof, such as ethanol, ethylene glycol or ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethylformamide, and epoxidized or non-epoxidized vegetable oils, such as epoxidized coconut or soya oil; or water.

Solid carriers which are used, for example for dusts and dispersible powders, are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acid or highly disperse absorbent polymers can also be added to improve the physical properties of the formulation. Granular adsorptive granule carriers can be porous types, for example pumice, crushed brick, sepiolite or bentonite, and non-adsorptive carrier materials can be, for example, calcite or sand. A large number of pregranulated materials of inorganic or organic nature, such as, in particular, dolomite or comminuted plant residues, can furthermore be used.

Surface-active compounds can be, depending on the nature of the active substance of the formula I to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

Soaps are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (C₁₀-C₂₂), for example the Na or K salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tallow oil. The fatty acid methyl-taurine salts are furthermore also to be mentioned.

More often, however, so-called synthetic surfactants are used, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and have an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals, for example the Na or Ca salt of ligninsulfonic acid, of dodecylsulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also include the salts of sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having 8-22 C. Atoms. Alkylarylsulfonates are, for example, the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.

Corresponding phosphates, for example salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids, can furthermore also be used.

Nonionic surfactants which can be used are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 8 carbon atoms in the alkyl radical of the alkylphenols.

Further suitable nonionic surfactants are the water-soluble polyethylene oxide adducts, containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups, on polypropylene glycol, ethylenediaminopolypropylene glycol and alkyl-polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of nonionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylenesorbitan, such as polyoxyethylenesorbitan trioleate, can furthermore also be used.

The cationic surfactants are, in particular, quaternary ammonium salts, which contain at least one alkyl radical having 8 to 22 C atoms as N-substituents and having lower halogenated or non-halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants which are conventionally used in the art of formulation and can also be used in the compositions according to the invention are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch [Surfactant Handbook]”, Carl Hanser Verlag, Munich/Vienna, 1981 and M. und J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations as a rule comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by, weight, of a surfactant.

While concentrated compositions tend to be preferred as commercial goods, the end user as a rule uses dilute compositions.

The compositions can also comprise further additives, such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and also fertilizers or other active substances.

Preferred formulations have, in particular, the following composition:

(%=per cent by weight)

Emulsifiable concentrates: Active substance: 1 to 90%, preferably 5 to 50% Surface-active agent: 5 to 30%, preferably 10 to 20% Solvent: 15 to 94%, preferably 70 to 85%

Emulsifiable concentrates: Active substance: 1 to 90%, preferably 5 to 50% Surface-active agent: 5 to 30%, preferably 10 to 20% Solvent: 15 to 94%, preferably 70 to 85%

Emulsifiable concentrates: Active substance: 1 to 90%, preferably 5 to 50% Surface-active agent: 5 to 30%, preferably 10 to 20% Solvent: 15 to 94%, preferably 70 to 85%

Emulsifiable concentrates: Active substance: 1 to 90%, preferably 5 to 50% Surface-active agent: 5 to 30%, preferably 10 to 20% Solvent: 15 to 94%, preferably 70 to 85%

Emulsifiable concentrates: Active substance: 1 to 90%, preferably 5 to 50% Surface-active agent: 5 to 30%, preferably 10 to 20% Solvent: 15 to 94%, preferably 70 to 85%

The active substances of the formula I are as a rule employed successfully on the plants or their environment with rates of application of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the required action can be determined by experiments. It depends on the nature of the action, the stage of development of the crop plants and of the weeds, and the application (location, time, method), and can vary within wide ranges, determined by these parameters.

The compounds of the formula I are distinguished by herbicidal and growth-inhibiting properties, which enable them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantations, oilseed rape, maize and rice, and for non-selective weed control.

Crops are also to be understood as including those which have been made tolerant towards herbicides and herbicide classes by conventional breeding or genetic engineering methods. The weeds to be controlled can be both mono- and dicotyledon weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

The following examples illustrate the invention further, without limiting it.

Preparation Examples EXAMPLE H1 Preparation of 1-(2-benzol[-b-]thienyl)-3,5-dichlorothiatriazine

A 1.6 M solution of n-butyllithium in hexane (107 ml) is added dropwise to a solution of 22.8 g of benzo[-b-]thiophene (0.17 mol) in 200 ml of absolute tetrahydrofuran at a temperature of −70° C., with intensive stirring and cooling. The resulting mixture is stirred at a temperature of −70° C. for 30 minutes. After adding a portion of 23.2 g of ZnCl₂ (0.17 mol) and waiting for the exothermic reaction, the mixture is warmed to 0° C. in the course of 1 hour and then cooled to −60° C. A solution of 34.7 g of trichlorothiatriazine (0.17 mol) in 50 ml of tetrahydrofuran is added dropwise, while stirring and cooling. After the mixture has beer stirred at −70° C. for 1 hour, the cooling bath is removed. The reaction mixture is diluted with water at 15° C., crystals precipitating out. The organic solvent is evaporated and the suspension is separated off with a suction filter. After the residue has been rinsed with water and pentane and dried, 1-(2-benzo[-b-]thienyl)-3,5-dichlorothiatriazine is obtained in the form of pale grey crystals having a melting point of 122-123° C.

EXAMPLE H2 Preparation of 3-amino-5-chloro-1-(2-furyl)-thiatriazine

Ammonia is passed into a solution of 3,5dichloro-1-(2-furyl)-thiatriazine (9.44 g, 0.04 mol) in 150 ml of tetrahydrofuran at a temperature of 20° C., while stirring vigorously. When the reaction is complete, the suspension is separated off with a suction filter, and the residue is rinsed with tetrahydrofuran and diethyl ether, subsequently stirred in water, filtered through a suction filter and then dried. 3-Amino-5chloro-1-(2-furyl)-thiatriazine is obtained in the form of white crystals which have a melting point of 215° C. (decomposition).

EXAMPLE H3 Preparation of 3-amino-1-(2-benzo[-b-]furyl)-5-(2-methoxy-4-hydroxycarbonylphenoxy)-thiatriazine

2N sodium hydroxide solution (10.5 ml, 0.021 mol) and 1.5 g of trimethylamine solution (40% in water) are added to a mixture of 2.66 g of 3-amino-1-(2-benzo[-b-]furyl)-5-chloro-thiatriazine (0.010 mol), 80 ml of dichoromethane and 1.85 g of vanillic acid (0.011 mol). The mixture is then stirred at a temperature of 20° C. for 18 hours. Thereafter, the dichoromethane is distilled off in vacuo and 300 ml of water and 1 ml of 2N sodium hydroxide solution are added to the residue. The mixture is introduced onto a suction filter provided with an inert adsorption material (for example Hyflo, silica gel), and the filtrate is then brought to pH 3-4 by means of 2N hydrochloric acid. Crystals precipitate out during this operation. The suspension is separated off with a suction filter and the residue is rinsed with water and then ether and dried. After recrystallization from acetonitrile/tetrahydrofuran (4:1), 3-amino-1-(2-benzo[-b-]furyl)-5-(2-methoxy-4-hydroxycarbonylphenoxy)-thiatriazine is obtained in the form of white crystals which have a melting point of 185° C. (decomposition).

EXAMPLE H4 Preparation of 3,5-dichloro-1-(2-(5-trimethylsilyl)-thienyl)-thiatriazine

A small amount (one spatula-tip) of AlCl₃ is added to a solution of 5.71 g of 2,5-bistrimethylsilylthiophene (0.025 mol) and 5.11 g of trichlorothiatriazine (0.025 mol) in 55 ml of absolute dichloromethane at a temperature of 24° C. under a nitrogen atmosphere. The colour of the reaction mixture changes from yellow to red during the course of the exothermic reaction. After the starting materials have been converted, the reaction mixture is evaporated in vacuo, the oily residue is dissolved in a mixture of hexane and dichloromethane, the solution is filtered through silica gel with a suction filter and the silica gel column is rinsed with diethyl ether. The filtrate is concentrated, white crystals of 3,5-dichloro-1-(2-(5-trimethylsilyl)-thienyl)-thiatriazine, which have a melting point of 114-116° C. (decomposition) being isolated.

The nomenclature used in the following is based on the numbering shown below:

The compounds listed in the following tables can also be prepared in an analogous manner.

TABLE 1 Heteroaromatic ring Q_(i):

Q_(i) W₁ W₂ W₃ W₄ Heterocyclic radical Q₁ CR₂₁ CR₂₂ CR₂₃ NR₂₄ 1H-Pyrrol-2-yl Q₂ CR₂₁ CR₂₂ CR₂₃ O 2-Furyl Q₃ CR₂₁ CR₂₂ O CR₂₄ 3-Furyl Q₄ CR₂₁ CR₂₂ CR₂₃ S 2-Thienyl Q₅ CR₂₁ CR₂₂ N NR₂₄ 2H-Pyrazol-3-yl Q₆ CR₂₁ CR₂₂ NR₂₃ N 1H-Pyrazol-3-yl Q₇ CR₂₁ N NR₂₃ CR₂₄ 1H-Pyrazol-4-yl Q₈ N CR₂₂ CR₂₃ NR₂₄ 1H-imidazol-2-yl Q₉ CR₂₁ CR₂₂ O N Isoxazol-3-yl Q₁₀ CR₂₁ O CR₂₃ N Oxazol-4-yl Q₁₁ O CR₂₂ CR₂₃ N Oxazol-2-yl Q₁₂ CR₂₁ CR₂₂ N O Isoxazol-5-yl Q₁₃ CR₂₁ 0 N CR₂₄ Isoxazol-4-yl Q₁₄ O CR₂₂ N CR₂₄ Oxazol-5-yl Q₁₅ CR₂₁ CR₂₂ S N Isothiazol-3-yl Q₁₆ CR₂₁ S CR₂₃ N Thiazol-4-yl Q₁₇ S CR₂₂ CR₂₃ N Thiazol-2-yI Q₁₈ CR₂₁ CR₂₂ N S Isothiazol-5-yl Q₁₉ CR₂₁ S N CR₂₄ Isothiazol-4-yl Q₂₀ S CR₂₂ N CR₂₄ Thiazol-5-yl Q₂₁ CR₂₁ N N NR₂₄ 3H-[1,2,3]-Triazol-4-yl Q₂₂ CR₂₁ N NR₂₃ N 2H-[1,2,3]-Triazol-4-yl Q₂₃ CR₂₁ NR₂₂ N N 1H-[1,2,3]-Triazol-4-yl Q₂₄ N CR₂₂ N NR₂₄ 2H-[1,2,4]-Triazol-3-yl Q₂₅ N CR₂₂ NR₂₃ N 1H-[1,2,4]-Triazol-3-yl Q₂₆ NR₂₁ CR₂₂ N N 4H-[1,2,4]-Triazol-3-yl Q₂₇ CR₂₁ O N N [1,2,3]Oxadiazol-4-yl Q₂₈ O CR₂₂ N N [1,3,4]Oxadiazol-2-yl Q₂₉ CR₂₁ N O N Furazan-3-yl Q₃₀ O N CR₂₃ N [1,2,4]Oxadiazol-5-yl Q₃₁ N O CR₂₃ N [1,2,4]Oxadiazol-3-yl Q₃₂ CR₂₁ N N O [1,2,3]Oxadiazol-5-yl Q₃₃ CR₂₁ S N N [1,2,3]Thiadiazol-4-yl Q₃₄ S CR₂₂ N N [1,3,4]Thiadiazol-2-yl Q₃₅ CR₂₁ N S N [1,2,5]Thiadiazol-3-yl Q₃₆ S N CR₂₃ N [1,2,4]Thiadiazol-5-yl Q₃₇ N S CR₂₃ N [1,2,4]Thiadiazol-3-yl Q₃₈ CR₂₁ N N S [1,2,3]Thiadiazol-5-yl Q₃₉ N N N NR₂₄ 1H-Tetrazol-5-yl Q₄₀ N N NR₂₃ N 2H-Tetrazol-5-yl Q₄₁ N N N O [1,2,3,4]Oxatriazol-5-yl Q₄₂ N N O N [1,2,3,5]Oxatriazol-4-yl Q₄₃ N N N S [1,2,3,4]Thiatriazol-5-yl Q₄₄ N N S N [1,2,3,5]Thiatriazol-4-yl

TABLE 2 Compounds of the formula Ia: (Ia)

Comp. No. Q_(i) R₂₁ R₂₂ R₂₃ R₂₄ XR₄ 2.001 Q₁ H —CH═CH—CH═N— CH₃

2.002 Q₁ CH₃ —C(Cl)═CH—CH═N— COCH₃

2.003 Q₁ —S—CH═CH— H 4—CH₃—C₆H₄

2.004 Q₁ —CH═CH—S— H 4—CH₃—C₆H₄

2.005 Q₂ H CH₃ H —

2.006 Q₂ H H H —

2.007 Q₂ H H —CH═CHCH₃ —

2.008 Q₂ H —CH═CH—CH═CH— —

2.009 Q₂

H H —

2.010 Q₂ H H SCH₃ —

2.011 Q₂ H H COOCH₃ —

2.012 Q₂ H H —CH═CH₂ —

2.013 Q₂ H H S(O)CH₃ —

2.014 Q₂ H H Si(CH₃)₃ —

2.015 Q₂ H —C(Cl)═CH—C(Cl)═CH— —

2.016 Q₂ H H COCH₃ —

2.017 Q₂ H H OCH₃ —

2.018 Q₂ H H Cl —

2.019 Q₂ H —C(OCH₃)═CH— CH═CH— —

2.020 Q₂ CH₃

—

2.021 Q₂ H —C(CH₃)═CH—CH═CH— —

2.022 Q₂ H —CH═CH—CH═C(CH₃)— —

2.023 Q₂ H H —C≡CH —

2.024 Q₂ OH —CH═CH—CH═CH— —

2.025 Q₂ H —CH═CH—CH═CH— —

2.026 Q₂ CH₃ —CH═C(CH₃)—C(CH₃)═CH— —

2.027 Q₂ H H H —

2.028 Q₂ CH₃ H H —

2.029 Q₂ H H C₂H₅ —

2.030 Q₂ Cl H H —

2.031 Q₂ H H n-C₆H₁₃ —

2.032 Q₂ H H CH₃ —

2.033 Q₂ —CH₂—C(CH₃)═C(CH₃)—CH₂— H —

2.034 Q₂ H H Sn(n-C₄H₉)₃ —

2.035 Q₂ H CH₃ H —

2.036 Q₂ H H SO₂CH₃ —

2.037 Q₂ —CH═C(CH₃)—C(CH₃)—CH— H —

2.038 Q₂ H H C₂H₅ —

2.039 Q₂ H H H —

2.040 Q₂ H H t-C₄H₉ —

2.041 Q₂ H H n-C₄H₉ —

2 042 Q₂ H H I —

2.043 Q₂ H H SCH₃ —

2.044 Q₂ H H B(OH)₂ —

2.045 Q₂ H H OCH₃ —

2.046 Q₂ H —CH═CH—CH═CH— —

2.047 Q₂ H —CO—NH—CH═CH— —

2.048 Q₂ H CH₃ F —

2.049 Q₂ OCH₃ H H —

2.050 Q₃ H H — CH₃

2.051 Q₃ H H — CON(C₂H₅)₂

2.052 Q₃ H H — Cl

2.053 Q₃ H H — OCH₃

2.054 Q₃ H Si(CH₃)₃ — CON(C₂H₅)₂

2.055 Q₃ H H — CH₂OCH₃

2.056 Q₃ —CH═CH—CH═CH— — CON(C₂H₅)₂

2.057 Q₃ CONH-t- C₄H₉ CH₃ — CH₃

2.058 Q₂ H H

—

2.059 Q₃ —CH═CH—CH═CH— — CH₂N(CH₃)2

2.060 Q₃ —CH═CH—CH═CH— —

2.061 Q₄ H H H —

2.062 Q₄ H —CH═CH—CH═CH— —

2.063 Q₄ H CH₃ F —

2.064 Q₄ OCH₃ H H —

2.065 Q₄ H —CH═CH—CH═CH— —

2.066 Q₄ H H t-C₄H₉ —

2.067 Q₄ H H n-C₄H₉ —

2.068 Q₄ H H H —

2.069 Q₄ H H CH₃ —

2.070 Q₄ CH₃ H H —

2.071 Q₄ H H C₂H₅ —

2.072 Q₄ Cl H H —

2.073 Q₄ H H n-C₆H₁₃ —

2.074 Q₄ H H Si(CH₃)₃ —

2.075 Q₄ H H Sn(n-C₄H₉)₃ —

2.076 Q₄ H H H —

2.077 Q₄ H H t-C₄H₉ —

2.078 Q₄ H H I —

2.079 Q₄ H H B(OH)₂ —

2.080 Q₄ H H 2-thienyl —

2.081 Q₄ H CH₃ H —

2.082 Q₄ CH₃ H H —

2.083 Q₄ —CH₂—CH₂—CH₂— C(OCH₃)₂— SCH₃ —

2.084 Q₄ H H C₂H₅ —

2.085 Q₄ H

—

2.086 Q₄ H H COCH₃ —

2.087 Q₄

SCH₃ —

2.088 Q₄ H H CH₃ —

2.089 Q₄ H

—

2.090 Q₄ H —CH═CH—CH═CH— —

2.091 Q₄ CH₃ —C(CH₃)═C(SCH₃)—S— — SC₆H₅ 2.092 Q₄ H

—

2.093 Q₄ H H COOCH₃ —

2.094 Q₄ H H 2-thienyl —

2.095 Q₄ CH₃

—

2.096 Q₄ H —S—CH═CH— —

2.097 Q₄ H —CH═CH—CH═CH— —

2.098 Q₄ H H —C≡CH —

2.099 Q₄ CH₃ —CH═N—CH═N— —

2.100 Q₄ CH₃ —N═CH—N═CH— —

2.101 Q₄ CH₃

—

2.102 Q₄ H H —CH═CH₂ —

2.103 Q₄ H H Si(CH₃)₃ —

2.104 Q₄ H

—

2.105 Q₄ H H C₂H₅ —

2.106 Q₄ H

—

2.107 Q₄ H H —CH═CHCH₃ —

2.108 Q₄ H

—

2.109 Q₄ C₆H₅

—

2.110 Q₄ H H CH₃ —

2.111 Q₄ —CH₂—C(CH₃)₂—CH═C(OCH₃)— SCH₃ — OCH₂CF₃ 2.112 Q₄ CH₃ —C(CH₃)═CH—S— —

2.113 Q₄ H H n-C₆H₁₃ —

2.114 Q₄ CH₃

—

2.115 Q₄ H H SO₂CH₃ —

2.116 Q₄ CH₃

—

2.117 Q₄ Si(CH₃)₃ H H —

2.118 Q₄ CH₃

—

2.119 Q₄ H

—

2.120 Q₄ H H n-C₆H₁₃ —

2.121 Q₄ CH₃

—

2.122 Q₄ H

—

2.123 Q₄ CH₃

—

2.124 Q₄ CH₃

—

2.125 Q₄ H

—

2.126 Q₄ H CH₃ H —

2.127 Q₄ H

— OC₆H₅ 2.128 Q₄ H

—

2.129 Q₄ H

—

2.130 Q₄ H H I —

2.131 Q₄ H

—

2.132 Q₄ H H S(O)CH₃ —

2.133 Q₄ H —CH═CH—CH═C(CH₃)— —

2.134 Q₄ —(CH₂)₂NH₂ —CH═CH— C(OCH₃)═CH— —

2.135 Q₄ —(CH₂)₂N(CH₃)₂ —C(OCH₃)═CH— CH═CH— —

2.136 Q₄ H H B(OH)₂ —

2.137 Q₄ —(CH₂)₂OH —CH═CH—CH═CH— —

2.138 Q₄ —CH₂SH —CH═CH—CH═CH— —

2.139 Q₄ CH₃ —CH═CF—CH═CH— — OCH₂CF₃ 2.140 Q₄ H

— SCH₂C₆H₅ 2.141 Q₄ H H 2-thienyl —

2.142 Q₄ OCH₃

— OC₆H₅ 2.143 Q₄ H H SCH₃ —

2.144 Q₄ (CH₂)₂OCOCH₃

— OCH₂C₇F₁₅ 2.145 Q₄ H H Sn(CH₃)₃ —

2.146 Q₄ CH₂CON(CH₃)2 —CH═CH— C(OCH₃)═CH— —

2.147 Q₄ H CH₃ H —

2.148 Q₄

—CH═CH—CH═CH— —

2.149 Q₄ H H OCH₃ —

2.150 Q₄ H —C(OH)═CH—CH═CH— —

2.151 Q₄ H H Sn(n-C₄H₉)₃ —

2.152 Q₄ CH₃ —CH═CH—CH═CH— —

2.153 Q₄ CH₂CO₂H —CH═CH—CH═CH— —

2.154 Q₄ CH₂CO₂C₂H₅ —CH═C(Cl)—CH═CH— —

2.155 Q₄ CH₃ —CH═C(Cl)—CH═CH— —

2.156 Q₄ H —CH═C(CH₃)—CH═CH— —

2.157 Q₄ H H Cl —

2.158 Q₄ CH₃ —CH═C(CH₃)—CH═CH— —

2.159 Q₄ H Si(CH₃)₃ H —

2.160 Q₄ NHC₄H₉ —CH═CH—CH═CH— —

2.161 Q₄ CH₂N(CH₃)₂ —CH═CH—CH═CH— —

2.162 Q₄

—CH═CH—CH═CH— —

2.163 Q₄ H H n-C₄H₉ —

2.164 Q₅ H H — C₆H₅

2.165 Q₅ H CH₃ — C₆H₅

2.166 Q₅ H CH₃ — CH₂OCH₃

2.167 Q₅ C₆H₅ CH₃ — CON(CH₃)₂

2.168 Q₅ —CH═CH—CH═CH— — CH₃

2.169 Q₅ H C₂H₅ — 2-Cl—C₆H₄

2.170 Q₅ H 3-(NH₂)—C₆H₄ — CH₃

2.171 Q₅ H C(OCH₃)₃ — i-C₃H₇

2.172 Q₅ H CH₃ — t-C₄H₉

2.173 Q₅ H SCH₃ — t-C₄H₉

2.174 Q₅ H 2- Thiazolyl — CH₃

2.175 Q₅

— CH₃

2.176 Q₅ H 3-Cl—C₆H₄ — CH₂OC₂H₅

2.177 Q₅ H CF₃ — CH₃

2.178 Q₅ H CH₃ — C₆H₅

2.179 Q₇ H — C₆H₅ H

2.180 Q₇ C₆H₅ — CH₃ H

2.181 Q₇ H — CH₃ C₆H₅

2.182 Q₇ CH₃ —

CH₃

2.183 Q₇ H — CH₃ OCH₃

2.184 Q₇ OCH₃ — CH₃ H

2.185 Q₇ N(CH₃)₂ — t-C₄H₉ CH₃

2.186 Q₇ CH₃ — t-C₄H₉ N(CH₃)₂

2.187 Q₈ — H H CH₂C₆H₅

2.188 Q₈ — H H SO₂C₆H₅

2.189 Q₈ — H H COO-t-C₄H₉

2.190 Q₈ — H H CONHt- C₄H₉

2.191 Q₈ — H H C₆H₅

2.192 Q₈ — H H CH₃

2.193 Q₈ — —CH═CH—CH═CH— n-C₃H₇

2.194 Q₈ — Cl Cl CH₂C₆H₅

2.195 Q₈ — H H CONHCH₃

2.196 Q₈ — —CH═CH—CH═CH— CO-t-C₄H₉

2.197 Q₈ — —CH═CH—CH═CH— CONHt- C₄H₉

2.198 Q₈ — CH₃ CH₃ CH₂OCH₃

2.199 Q₈ — —CH₂—CH₂—CH₂—CH₂— CON(CH₃)₂

2.200 Q₈ — H H SO₂N(CH₃)₂

2.201 Q₁₁ — —CH═C(CH₃)—CH═CH— —

2.202 Q₁₁ — —CH═CH—C(CH₃)═CH— —

2.203 Q₁₁ — —CH═CH—C(Cl)═CH— —

2.204 Q₁₁ — —CH═CH—CH═CH— —

2.205 Q₁₁ — 3-NH₂—C₆H₄ H —

2.206 Q₁₁ — C₆H₅ H —

2.207 Q₁₁ — 2-Cl—C₆H₄ H —

2.208 Q₁₁ — 4-F—C₆H₄ H —

2.209 Q₁₁ — 2-Furyl H —

2.210 Q₁₁ — 4-Tolyl H —

2.211 Q₁₁ — 4-Anisyl H —

2.212 Q₁₁ — 2-Thienyl H —

2.213 Q₁₁ —

H —

2.214 Q₁₁ — 4-CF₃— C₆H₄ CO₂C₂H₅ — OC₈H₁₇ 2.215 Q₁₁ — C₆H₅ CO₂C₂H₅ —

2.216 Q₁₁ — 2,4- Dichloro- phenyl CO₂C₂H₅ —

2.217 Q₁₁ — 3-Cl—C₆H₄ CO₂C₂H₅ —

2.218 Q₁₁ — t-C₄H₉ CO₂C₂H₅ —

2.219 Q₁₃ H — — H

2.220 Q₁₃ NHCOOt- C₄H₉ — — CH₃

2.221 Q₁₃ CH₃ — — CH₃

2.222 Q₁₃ C₆H₅ — — CH₃

2.223 Q₁₃ H — — CH₃

2.224 Q₁₃ H — — 2-Thienyl

2.225 Q₁₃ CH₃ — — CON(CH₃)₂

2.226 Q₁₃ CH₃ — — CH₂OC₂H₅

2.227 Q₁₃ H — — CH(OC₂H₅)₂

2.228 Q₁₃ H — —

2.229 Q₁₃

— — CH₃

2.230 Q₁₃ C₆H₅ — — 2-Furyl

2.231 Q₁₃

— — 4-Cl—C₆H₄

2.232 Q₁₃ C₆H₅ — — 2,4- Dichloro- phenyl

2.233 Q₁₃ CH₃ — —

2.234 Q₁₃ (CH₂)₅Cl — — CH₂OCH₃

2.235 Q₁₃ N(CH₃)C₆H₅ — — t-C₄H₉ OCH(CF₃)₂ 2.236 Q₁₃

— — CH₃

2.237 Q₁₃ CH₃ — —

2.238 Q₁₃ CH₃ — — CF₃ OCH₂C₇F₁₅ 2.239 Q₁₆ OC₂H₅ — CH₃ —

2.240 Q₁₈ OH — i-C₃H₇ —

2.241 Q₁₅ OCH₃ — t-C₄H₉ —

2.242 Q₁₇ — H H — S-i-C₃H₇ 2.243 Q₁₇ — H CH₃ — OCH(CF₃)₂ 2.244 Q₁₇ — H C₆H₅ — OCH₂C₆F₅ 2.245 Q₁₇ — H CN — OC₆H₅ 2.246 Q₁₇ — —CH═CH—CH═CH— —

2.247 Q₁₇ — —CF═CH—CH═CH— —

2.248 Q₁₇ — —CH═CH—CH═CF— —

2.249 Q₁₇ — —CH═CH—CCl═CH— —

2.250 Q₁₇ — —CH═CH—CH═CH— —

2.251 Q₁₇ — Si(CH₃)₃ H — OCH₂C₃F₇ 2.252 Q₁₇ — CH₃ H —

2.253 Q₁₇ — C₆H₅ H —

2.254 Q₁₇ — Si(CH₃)₃ CH₂OCH₃ —

2.255 Q₁₈ CH₂C₆H₅ H — —

2.256 Q₁₈ H NHCOO- t-C₄H₉ — —

2.257 Q₁₈ C₆H₅ NHCO-t- C₄H₉ — —

2.258 Q₁₆ C₆H₅ CONHN (CH₃)₂ — —

2.259 Q₁₈ —CH═CH—CH═CH— — —

2.260 Q₁₈ H H — —

2.261 Q₁₈ H CH₃ — —

2.262 Q₁₈ NH₂ H — —

2.263 Q₁₈ NH₂ CH₃ — —

2.264 Q₁₈ CON(C₂H₅)₂ H — —

2.265 Q₁₈ NHCOOC₂H₅ H — —

2.266 Q₁₈ NHCOC₆H₅ H — —

2.267 Q₁₈ C₆H₅ SCH₃ — —

2.268 Q₁₈

CH₃ — —

2.269 Q₁₈ 4-Tolyl SCH₃ — —

2.270 Q₁₈

H — —

2.271 Q₁₈ H O-n-C₄H₉ — —

2.272 Q₁₈ —CH₂—(CH₂)₃—CH₂— — —

2.273 Q₁₈ H O-i-C₃H₇ — —

2.274 Q₁₈ —CH₂—(CH₂)₄—CH₂— — —

2.275 Q₁₈ CH₃ 4-Tolyl — —

2.276 Q₁₈ H 2-Tolyl — —

2.277 Q₁₈ H CBr₃ — — OCH₂CH(CF₃)₂ 2.278 Q₁₈ 4-Cl—C₆H₄ H — —

2.279 Q₁₈ —CH═CH—S— — —

2.280 Q₁₈ CH(OC₂H₅)₂ CH₃ — —

2.281 Q₁₈ 4-Cl—C₆H₄ CON(CH₃)₂ — —

2.282 Q₁₈ —S—CH═CH— — —

2.283 Q₁₈ H 4-Cl—C₆H₄ — —

2.284 Q₂₀ — CH₃ — CH₃

2.285 Q₂₀ — NHCOO- t-C₄H₉ — H

2.286 Q₂₀ — NHCOO- t-C₄H₉ — CH₃

2.287 Q₂₀ — i-C₄H₉ — H

2.288 Q₂₀ — i-C₃H₇ — CH₃

2.289 Q₂₀ — C₂H₅ — CH₃

2.290 Q₂₀ — NH₂ —

2.291 Q₂₀ — NH₂ — 4-Cl—C₆H₄

2.292 Q₂₀ — CH₃ — t-C₄H₉

2.293 Q₂₀ — s-C₄H₉ — H

2.294 Q₂₀ — i-C₄H₉ — CH₃ O-i-C₃H₇ 2.295 Q₂₀ — Si(CH₃)₃ — H

2.296 Q₂₀ — n-C₃H₇ — H O-c-C₆H₁₁ 2.297 Q₂₀ — CH₃ — CH₃

2.298 Q₂₀ — OC₂H₅ — H

2.299 Q₂₀ — CH₃ — CN

2.300 Q₂₀ — H — C₆H₅

2.301 Q₂₀ — CH₃ —

2.302 Q₂₀ — CH₃ — 3-Pyridyl

2.303 Q₂₀ — C₆H₅ — CONHCH₃

2.304 Q₂₀ — NHCOCH₃ — CF₃

2.305 Q₂₁ H — — C₆H₅

2.306 Q₂₁ CH₂OCH₃ — — C₆H₅

2.307 Q₂₁ CH₃ — — 4-Cl—C₆H₄

2.308 Q₃₀ — — C₆H₅ —

2.309 Q₃₀ — — n-C₄H₉ —

2.310 Q₃₃ C₆H₅ — — —

2.311 Q₃₃ t-C₄H₉ — — —

2.312 Q₃₃ i-C₃H₇ — — —

2.313 Q₃₃ C₂H₅ — — —

2.314 Q₃₃ CH₃ — — —

2.315 Q₃₃ OCH₃ — — —

2.316 Q₃₃ O-n-C₄H₉ — — —

2.317 Q₃₃ N(C₂H₅)₂ — — —

2.318 Q₃₃ SCH₃ — — —

2.319 Q₃₃ S-c-C₆H₁₁ — — —

2.320 Q₃₃

— — — OC₈H₁₇ 2.321 Q₃₃

— — —

2.322 Q₃₃

— — —

2.323 Q₃₉ — — — CH₃

2.324 Q₃₉ — — — C₆H₅

2.325 Q₃₉ — — — n-C₄H₉

2.326 Q₄ H H OCH₃ —

2.327 Q₄ H H Cl —

2.328 Q₂₀ — Cl — H

2.329 Q₂₀ — O—CH₂CF₃ — H

2.330 Q₂₀ — —CN — H

2.331 Q₂₀ —

— H

2.332 Q₂₀ —

— H

2.333 Q₂₀ —

— H

2.334 Q₂₀ — Cl — H OCH₂CF₃ 2.335 Q₂₀ — OCH₂CF₃ — H OCH₂CF₃ 2.336 Q₂₀ — Cl — H

2.337 Q₂ CH₃

—

TABLE 3 Compounds of the formula Ib: Ib

Comp. No. Q_(i) R₂₁ R₂₂ R₂₃ R₂₄ XR₄ 3.001 Q₁ H —CH═CH—CH═N— CH₃

3.002 Q₁ CH₃ —C(Cl)═CH—CH═N— COCH₃

3.003 Q₁ —S—CH═CH— H 4-CH₃—C₆H₄

3.004 Q₁ —CH═CH—S— H 4-CH₃—C₆H₄

3.005 Q₂ H CH₃ H —

3.006 Q₂ H H H —

3.007 Q₂ H H —CH═CHCH₃ —

3.008 Q₂

H H —

3.009 Q₂ H H SCH₃ —

3.010 Q₂ H H COOCH₃ —

3.011 Q₂ H H —CH═OH₂ —

3.012 Q₂ H —C(Cl)═CH—C(Cl)═CH— —

3.013 Q₂ H H OCH₃ —

3.014 Q₂ H H Cl —

3.015 Q₂ H —C(OCH₃)═CH—CH═CH— —

3.016 Q₂ CH₃

—

3.017 Q₂ H —C(CH₃)═CH—CH═CH— —

3.018 Q₂ H —CH═CH—CH═C(CH₃)— —

3.019 Q₂ H H —C≡CH —

3.020 Q₂ H —CH═CH—CH═CH— —

3.021 Q₂ CH₃ —CH═C(CH₃)—C(CH₃)═CH— —

3.022 Q₂ H H H —

3.023 Q₂ CH₃ H H —

3.024 Q₂ Cl H H —

3.025 Q₂ H H n-C₆H₁₃ —

3.026 Q₂ H H CH₃ —

3.027 Q₂ —CH₂—C(CH₃)═C(CH₃)—CH₂— H —

3.028 Q₂ H CH₃ H —

3.029 Q₂ H H SO₂CH₃ —

3.030 Q₂ —CH═C(CH₃)—C(CH₃)═CH— H —

3.031 Q₂ H H C₂H₅ —

3.032 Q₂ H H H —

3.033 Q₂ H H t-C₄H₉ —

3.034 Q₂ H H n-C₄H₉ —

3.035 Q₂ H H I —

3.036 Q₂ H H SCH₃ —

3.037 Q₂ H —CH═CH—CH═CH— —

3.038 Q₂ H CH₃ F —

3.039 Q₂ OCH₃ H H —

3.040 Q₃ H H — CH₃

3.041 Q₃ H H — CON(C₂H₅)₂

3.042 Q₃ H H — Cl

3.043 Q₃ H H — CH₂OCH₃

3.044 Q₃ —CH═CH—CH═CH— — CON(C₂H₅)₂ 3.045 Q₃ H H

—

3.046 Q₃ —CH═CH—CH═CH— — CH₂N(CH₃)₂

3.047 Q₃ —CH═CH—CH═CH— —

3.048 Q₄ H H H —

3.049 Q₄ H —CH═CH—CH═CH— —

3.050 Q₄ H CH₃ F —

3.051 Q₄ OCH₃ H H —

3.052 Q₄ H —CH═CH—CH═CH— —

3.053 Q₄ H H t-C₄H₉ —

3.054 Q₄ H H n-C₄H₉ —

3.055 Q₄ H H H —

3.056 Q₄ H H CH₃ —

3.057 Q₄ CH₃ H H —

3.058 Q₄ H H C₂H₅ —

3.059 Q₄ Cl H H —

3.060 Q₄ H H n-C₆H₁₃ —

3.061 Q₄ H H t-C₄H₉ —

3.062 Q₄ H H I —

3.063 Q₄ H H 2-thienyl —

3.064 Q₄ H CH₃ H —

3.065 Q₄ CH₃ H H —

3.066 Q₄ —CH₂—CH₂—CH₂—C(OCH₃)₂— SCH₃ —

3.067 Q₄ H H C₂H₅ —

3.068 Q₄ H

—

3.069 Q₄ H H COCH₃ —

3.070 Q₄

SCH₃ —

3.071 Q₄ H H CH₃ —

3.072 Q₄ H

—

3.073 Q₄ H —CH═CH—CH═CH— —

3.074 Q₄ CH₃ —C(CH₃)═C(SCH₃)—S— — SC₆H₅ 3.075 Q₄ H

—

3.076 Q₄ H H COOCH₃ —

3.077 Q₄ H H 2-thienyl —

3.078 Q₄ CH₃

—

3.079 Q₄ H —CH═CH—CH═CH— —

3.080 Q₄ H H —C≡CH —

3.081 Q₄ CH₃ —CH═N—CH═N— —

3.082 Q₄ CH₃ —N═CH—N═CH— —

3.083 Q₄ H H —CH═CH₂ —

3.084 Q₄ H H C₂H₅ —

3.085 Q₄ H H —CH═CHCH₃ —

3.086 Q₄ H H CH₃ —

3.087 Q₄ —CH₂—C(CH₃)₂—CH═C(OCH₃)— SCH₃ — OCH₂CF₃ 3.088 Q₄ CH₃ —C(CH₃)═CH—S— —

3.089 Q₄ H H n-C₆H₁₃ —

3.090 Q₄ H H SO₂CH₃ —

3.091 Q₄ H H n-C₆H₁₃ —

3.092 Q₄ H CH₃ H —

3.093 Q₄ H H I —

3.094 Q₄ H —CH═CH—CH═C(CH₃)— —

3.095 Q₄ —(CH₂)₂NH₂ —CH═CH—C(OCH₃)═CH— —

3.096 Q₄ —(CH₂)₂N(CH₃)₂ —C(OCH₃)═CH—CH═CH— —

3.097 Q₄ CH₃ —CH═CF—CH═CH— — OCH₂CF₃ 3.098 Q₄ H H 2-thienyl —

3.099 Q₄ OCH₃

— OC₆H₅ 3.100 Q₄ H H SCH₃ —

3.101 Q₄ CH₂CON(CH₃)₂ —CH═CH—C(OCH₃)═CH— —

3.102 Q₄ H CH₃ H —

3.103 Q₄ H H OCH₃ —

3.104 Q₄ H —C(OH)═CH—CH═CH— —

3.105 Q₄ H H Sn(n-C₄H₉)₃ —

3.106 Q₄ CH₃ —CH═CH—CH═CH— —

3.107 Q₄ CH₂CO₂H —CH═CH—CH═CH— —

3.108 Q₄ CH₂CO₂C₂H₅ —CH═C(Cl)—CH═CH— —

3.109 Q₄ CH₃ —CH═C(Cl)—CH═CH— —

3.110 Q₄ H —CH═C(CH₃)—CH═CH— —

3.111 Q₄ H H Cl —

3.112 Q₄ CH₃ —CH═C(CH₃)—CH═CH— —

3.113 Q₄ H H n-C₄H₉ —

3.114 Q₅ H H C₆H₅ —

3.115 Q₅ H CH₃ — C₆H₅

3.116 Q₅ H CH₃ — CH₂OCH₃

3.117 Q₅ C₆H₅ CH₃ — CON(CH₃)₂

3.118 Q₅ —CH═CH—CH═CH— — CH₃

3.119 Q₅ H C₂H₅ — 2-Cl—C₆H₄

3.120 Q₅ H CH₃ — t-C₄H₉

3.121 Q₅ H SCH₃ — t-C₄H₉

3.122 Q₅ H 2-Thiazolyl — CH₃

3.123 Q₅

— CH₃

3.124 Q₅ H 3-Cl—C₆H₄ — CH₂OC₂H₅

3.125 Q₅ H CF₃ — CH₃

3.126 Q₅ H CH₃ — C₆H₅

3.127 Q₇ H — C₆H₅ H

3.128 Q₇ C₆H₅ — CH₃ H

3.129 Q₇ H — CH₃ C₆H₅

3.130 Q₇ H — CH₃ OCH₃

3.131 Q₇ OCH₃ — CH₃ H

3.132 Q₇ N(CH₃)₂ — t-C₄H₉ CH₃

3.133 Q₇ CH₃ — t-C₄H₉ N(CH₃)₂

3.134 Q₈ — H H CH₂C₆H₅

3.135 Q₈ — H H SO₂C₆H₅

3.136 Q₈ — H H C₆H₅

3.137 Q₈ — H H CH₃

3.138 Q₈ — —CH═CH—CH═CH— n-C₃H₇

3.139 Q₈ — Cl Cl CH₂C₆H₅

3.140 Q₈ — CH₃ CH₃ CH₂OCH₃

3.141 Q₈ — —CH₂—CH₂—CH₂—CH₂— CON(CH₃)₂

3.142 Q₁₁ — —CH═C(CH₃)—CH═CH— —

3.143 Q₁₁ — —CH═CH—C(CH₃)═CH— —

3.144 Q₁₁ — —CH═CH—C(Cl)═CH— —

3.145 Q₁₁ — —CH═CH—CH═CH— —

3.146 Q₁₁ — C₆H₅ H —

3.147 Q₁₁ — 2-Cl—C₆H₄ H —

3.148 Q₁₁ — 2-Furyl H —

3.149 Q₁₁ — 2-Thienyl H —

3.150 Q₁₁ — 4-CF₃—C₆H₄ CO₂C₂H₅ — OC₈H₁₇ 3.151 Q₁₁ — C₆H₅ CO₂C₂H₅ —

3.152 Q₁₁ — 2,4-Dichlorophenyl CO₂C₂H₅ —

3.153 Q₁₁ — 3-Cl—C₆H₄ CO₂C₂H₅ —

3.154 Q₁₁ — t-C₄H₉ CO₂C₂H₅ —

3.155 Q₁₃ H — — H

3.156 Q₁₃ CH₃ — — CH₃

3.157 Q₁₃ C₆H₅ — — CH₃

3.158 Q₁₃ H — — CH₃

3.159 Q₁₃ H — — 2-Thienyl

3.160 Q₁₃ CH₃ — — CON(CH₃)₂

3.161 Q₁₃ CH₃ — — CH₂OC₂H₅

3.162 Q₁₃ H — —

3.163 Q₁₃

— — CH₃

3.164 Q₁₃ C₆H₅ — — 2-Furyl

3.165 Q₁₃ C₆H₅ — — 2,4-Dichlorophenyl

3.166 Q₁₃ CH₃ — —

3.167 Q₁₃ (CH₂)₅Cl — — CH₂OCH₃

3.168 Q₁₃ N(CH₃)C₆H₅ — — t-C₄H₉ OCH(CF₃)₂ 3.169 Q₁₃

— — CH₃

3.170 Q₁₃ CH₃ — —

3.171 Q₁₃ CH₃ — — CF₃ OCH₂C₇F₁₅ 3.172 Q₁₆ OC₂H₅ — CH₃ —

3.173 Q₁₆ OCH₃ — t-C₄H₉ —

3.174 Q₁₇ — H H — S-i-C₃H₇ 3.175 Q₁₇ — H CH₃ — OCH(CF₃)₂ 3.176 Q₁₇ — H C₆H₅ — OCH₂C₆F₅ 3.177 Q₁₇ — H CN — OC₆H₅ 3.178 Q₁₇ — —CH═CH—CH═CH— —

3.179 Q₁₇ — —CF═CH—CH═CH— —

3.180 Q₁₇ — —CH═CH—CH═CF— —

3.181 Q₁₇ — —CH═CH—CCl═CH— —

3.182 Q₁₇ — —CH═CH—CH═CH— —

3.183 Q₁₇ — CH₃ H —

3.184 Q₁₈ CH₂C₆H₅ H — —

3.185 Q₁₈ —CH═CH—CH═CH— — —

3.186 Q₁₈ H H — —

3.187 Q₁₈ H CH₃ — —

3.188 Q₁₈ CON(C₂H₅)₂ H — —

3.189 Q₁₈ C₆H₅ SCH₃ — —

3.190 Q₁₈ 4-Tolyl SCH₃ — —

3.191 Q₁₈ —CH₂—(CH₂)₃—CH₂— — —

3.192 Q₁₈ H O-i-C₃H₇ — —

3.193 Q₁₈ CH₃ 4-Tolyl — —

3.194 Q₁₈ H 2-Tolyl — —

3.195 Q₁₈ 4-Cl—C₆H₄ H — —

3.196 Q₁₈ —CH═CH—S— — —

3.197 Q₁₈ 4-Cl—C₆H₄ CON(CH₃)₂ — —

3.198 Q₁₈ —S—CH═CH— — —

3.199 Q₁₈ H 4-Cl—C₆H₄ — —

3.200 Q₂₀ — CH₃ — CH₃

3.201 Q₂₀ — i-C₄H₉ — H

3.202 Q₂₀ — i-C₃H₇ — CH₃

3.203 Q₂₀ — C₂H₅ — CH₃

3.204 Q₂₀ — CH₃ — t-C₄H₉

3.205 Q₂₀ — CH₃ — CH₃

3.206 Q₂₀ — OC₂H₅ — H

3.207 Q₂₀ — CH₃ — CN

3.208 Q₂₀ — H — C₆H₅

3.209 Q₂₀ — CH₃ — 3-Pyridyl

3.210 Q₂₀ — C₆H₅ — CONHCH₃

3.211 Q₂₁ H — — C₆H₅

3.212 Q₂₁ CH₂OCH₃ — — C₆H₅

3.213 Q₂₁ CH₃ — — 4-Cl—C₆H₄

3.214 Q₃₀ — — C₆H₅ —

3.215 Q₃₀ — — n-C₄H₉ —

3.216 Q₃₃ C₆H₅ — — —

3.217 Q₃₃ t-C₄H₉ — — —

3.218 Q₃₃ i-C₃H₇ — — —

3.219 Q₃₃ C₂H₅ — — —

3.220 Q₃₃ OCH₃ — — —

3.221 Q₃₃ O-n-C₄H₉ — — —

3.222 Q₃₃ N(C₂H₅)₂ — — —

3.223 Q₃₃ SCH₃ — — —

3.224 Q₃₃ S-c-C₆H₁₁ — — —

3.225 Q₃₉ — — — CH₃

3.226 Q₃₉ — — — n-C₄H₉

3.327 Q₂₀ — Cl — H

3.328 Q₂₀ — O—CH₂CF₃ — H

3.329 Q₂₀ — —CN — H

3.330 Q₂₀ —

— H

3.331 Q₂₀ —

— H

3.332 Q₂₀ —

— H

3.333 Q₂₀ — Cl — H OCH₂CF₃ 3.334 Q₂₀ — OCH₂CF₃ — H OCH₂CF₃ 3.335 Q₂₀ — Cl — H

TABLE 4

Comp. No. Q_(i) R₂₁ R₂₂ R₂₃ R₂₄ 4.001 Q₁ H —CH═CH—CH═N— CH₃ 4.002 Q₁ CH₃ —C(Cl)═CH—CH═N— COCH₃ 4.003 Q₁ —S—CH═CH— H 4-CH₃—C₆H₄ 4.004 Q₁ —CH═CH—S— H 4-CH₃—C₆H₄ 4.005 Q₂ H CH₃ H — 4.006 Q₂ H H H — 4.007 Q₂ H H —CH═CHCH₃ — 4.008 Q₂ H —CH═CH—CH═CH— — 4.009 Q₂

H H — 4.010 Q₂ H H SCH₃ — 4.011 Q₂ H H COOCH₃ — 4.012 Q₂ H H —CH═CH₂ — 4.013 Q₂ H H S(O)CH₃ — 4.014 Q₂ H H Si(CH₃)₃ — 4.015 Q₂ H —C(Cl)═CH—C(Cl)═CH— — 4.016 Q₂ H H COCH₃ — 4.017 Q₂ H H OCH₃ — 4.018 Q₂ H H Cl 4.019 Q₂ H —C(OCH₃)═CH— — CH═CH— 4.020 Q₂ CH₃

— 4.021 Q₂ H —C(CH₃)═CH—CH═CH— — 4.022 Q₂ H —CH═CH—CH═C(CH₃)— — 4.023 Q₂ H H —C≡CH — 4.024 Q₂ OH —CH═CH—CH═CH— — 4.025 Q₂ CH₃ —CH═C(CH₃)—C(CH₃)═CH— — 4.026 Q₂ CH₃ H H — 4.027 Q₂ H H C₂H₅ — 4.028 Q₂ Cl H H — 4.029 Q₂ H H n-C₆H₁₃ — 4.030 Q₂ H H CH₃ — 4.031 Q₂ —CH₂—C(CH₃)═C(CH₃)—CH₂— H — 4.032 Q₂ H H Sn(n-C₄H₉)₃ — 4.033 Q₂ H H SO₂CH₃ — 4.034 Q₂ H H t-C₄H₉ — 4.035 Q₂ H H n-C₄H₉ — 4.036 Q₂ H H I — 4.037 Q₂ H H B(OH)₂ — 4.038 Q₂ H —CO—NH—CH═CH— — 4.039 Q₂ H CH₃ F — 4.040 Q₂ OCH₃ H H — 4.041 Q₃ H H — CH₃ 4.042 Q₃ H H — CON(C₂H₅)₂ 4.043 Q₃ H H — Cl 4.044 Q₃ H H — OCH₃ 4.045 Q₃ H Si(CH₃)₃ — CON(C₂H₅)₂ 4.046 Q₃ H H — CH₂OCH₃ 4.047 Q₃ —CH═CH—CH═CH— — CON(C₂H₅)₂ 4.048 Q₃ CONH-t-C₄H₉ CH₃ — CH₃ 4.049 Q₂ H H

— 4.050 Q₃ —CH═CH—CH═CH— — CH₂N(CH₃)₂ 4.051 Q₃ —CH═CH—CH═CH— —

4.052 Q₄ H H H — 4.053 Q₄ H —CH═CH—CH═CH— — 4.054 Q₄ H CH₃ F — 4.055 Q₄ OCH₃ H H — 4.056 Q₄ H H t-C₄H₉ — 4.057 Q₄ H H n-C₄H₉ — 4.058 Q₄ H H CH₃ — 4.059 Q₄ CH₃ H H — 4.060 Q₄ H H C₂H₅ — 4.061 Q₄ Cl H H — 4.062 Q₄ H H n-C₆H₁₃ — 4.063 Q₄ H H Si(CH₃)₃ — 4.064 Q₄ H H Sn(n-C₄H₉)₃ — 4.065 Q₄ H H I — 4.066 Q₄ H H B(OH)₂ — 4.067 Q₄ H H 2-thienyl — 4.068 Q₄ H CH₃ H — 4.069 Q₄ —CH₂—CH₂—CH₂— SCH₃ — C(OCH₃)₂— — 4.070 Q₄ H

4.071 Q₄ H H COCH₃ — 4.072 Q₄

SCH₃ — 4.073 Q₄ H

— 4.074 Q₄ CH₃ —C(CH₃)═C(SCH₃)—S— — 4.075 Q₄ H

— 4.076 Q₄ H H COOCH₃ — 4.077 Q₄ CH₃

— 4.078 Q₄ H —S—CH═CH— — 4.079 Q₄ H H —C≡CH — 4.080 Q₄ CH₃ —CH═N—CH═N— — 4.081 Q₄ CH₃ —N═CH—N═CH— — 4.082 Q₄ CH₃

— 4.083 Q₄ H H —CH═CH₂ — 4.084 Q₄ H

— 4.085 Q₄ H

— 4.086 Q₄ H H —CH—CHCH₃ — 4.087 Q₄ H

— 4.088 Q₄ C₆H₅

— 4.089 Q₄ —CH₂—C(CH₃)₂—CH═C(OCH₃)— SCH₃ — 4.090 Q₄ CH₃ —C(CH₃)═CH—S— — 4.091 Q₄ CH₃

— 4.092 Q₄ H H SO₂CH₃ — 4.093 Q₄ CH₃

— 4.094 Q₄ Si(CH₃)₃ H H — 4.095 Q₄ CH₃

— 4.096 Q₄ CH₃

— 4.097 Q₄ H

— 4.098 Q₄ CH₃

— 4.099 Q₄ CH₃

— 4.100 Q₄ H

— 4.101 Q₄ H

— 4.102 Q₄ H

— 4.103 Q₄ H

— 4.104 Q₄ H

— 4.105 Q₄ H H S(O)CH₃ — 4.106 Q₄ H —CH═CH—CH═C(CH₃)— — 4.107 Q₄ —(CH₂)₂NH₂ —CH═CH— — C(OCH₃)═CH— 4.108 Q₄ —(CH₂)₂N(CH₃)₂ —C(OCH₃)═CH— — CH═CH— 4.109 Q₄ —(CH₂)₂OH —CH═CH—CH═CH— — 4.110 Q₄ —CH₂SH —CH═CH—CH═CH— — 4.111 Q₄ CH₃ —CH═CF—CH═CH— — 4.112 Q₄ H

— 4.113 Q₄ OCH₃

— 4.114 Q₄ H H SCH₃ — 4.115 Q₄ H H Sn(CH₃)₃ — 4.116 Q₄ CH₂CON(CH₃)₂ —CH═CH— — C(OCH₃)═CH— 4.117 Q₄ H CH₃ H — 4.118 Q₄ H H OCH₃ — 4.119 Q₄ H —C(OH)═CH—CH═CH— — 4.120 Q₄ CH₃ —CH═CH—CH═CH— — 4.121 Q₄ CH₂CO₂H —CH═CH—CH═CH— — 4.122 Q₄ CH₂CO₂C₂H₅ —CH═C(Cl)—CH═CH— — 4.123 Q₄ CH₃ —CH═C(Cl)—CH═CH— — 4.124 Q₄ H —CH═C(CH₃)—CH═CH— — 4.125 Q₄ H H Cl — 4.126 Q₄ CH₃ —CH═C(CH₃)—CH═CH— — 4.127 Q₄ H Si(CH₃)₃ H — 4.128 Q₄ CH₂N(CH₃)₂ —CH═CH—CH═CH— — 4.129 Q₄

—CH═CH—CH═CH— — 4.130 Q₅ H H — C₆H₅ 4.131 Q₅ H CH₃ — C₆H₅ 4.132 Q₅ H CH₃ — CH₂OCH₃ 4.133 Q₅ C₆H₅ CH₃ — CON(CH₃)₂ 4.134 Q₅ —CH═CH—CH═CH— — CH₃ 4.135 Q₅ H C₂H₅ — 2-Cl—C₆H₄ 4.136 Q₅ H C(OCH₃)₃ — i-C₃H₇ 4.137 Q₅ H CH₃ — t-C₄H₉ 4.138 Q₅ H SCH₃ — t-C₄H₉ 4.139 Q₅ H 2-Thiazolyl — CH₃ 4.140 Q₅

— CH₃ 4.141 Q₅ H 3-Cl—C₆H₄ — CH₂OC₂H₅ 4.142 Q₅ H CF₃ — CH₃ 4.143 Q₇ H — C₆H₅ H 4.144 Q₇ C₆H₅ — CH₃ H 4.145 Q₇ H — CH₃ C₆H₅ 4.146 Q₇ CH₃ —

CH₃ 4.147 Q₇ H — CH₃ OCH₃ 4.148 Q₇ OCH₃ — CH₃ H 4.149 Q₇ N(CH₃)₂ — t-C₄H₉ CH₃ 4.150 Q₇ CH₃ — t-C₄H₉ N(CH₃)₂ 4.151 Q₈ — H H CH₂C₆H₅ 4.152 Q₈ — H H SO₂C₆H₅ 4.153 Q₈ — H H C₆H₅ 4.154 Q₈ — H H CH₃ 4.155 Q₈ — —CH═CH—CH═CH— n-C₃H₇ 4.156 Q₈ — Cl Cl CH₂C₆H₅ 4.157 Q₈ — H H CONHCH₃ 4.158 Q₈ — —CH═CH—CH═CH— CO-t-C₄H₉ 4.159 Q₈ — —CH═CH—CH═CH— CONHt-C₄H₉ 4.160 Q₈ — CH₃ CH₃ CH₂OCH₃ 4.161 Q₈ — —CH₂—CH₂—CH₂—CH₂— CON(CH₃)₂ 4.162 Q₈ — H H SO₂N(CH₃)₂ 4.163 Q₁₁ — —CH═C(CH₃)—CH═CH— — 4.164 Q₁₁ — —CH═CH—C(CH₃)═CH— — 4.165 Q₁₁ — —CH═CH—C(Cl)═CH— — 4.166 Q₁₁ — —CH═CH—CH═CH— 4.167 Q₁₁ — C₆H₅ H — 4.168 Q₁₁ — 2-Cl—C₆H₄ H — 4.169 Q₁₁ — 4-F—C₆H₄ H — 4.170 Q₁₁ — 2-Furyl H — 4.171 Q₁₁ — 4-Tolyl H — 4.172 Q₁₁ — 4-Anisyl H — 4.173 Q₁₁ — 2-Thienyl H — 4.174 Q₁₁ —

H — 4.175 Q₁₁ — 4-CF₃—C₆H₄ CO₂C₂H₅ — 4.176 Q₁₁ — C₆H₅ CO₂C₂H₅ — 4.177 Q₁₁ — 2,4-Dichlorophenyl CO₂C₂H₅ — 4.178 Q₁₁ — 3-Cl—C₆H₄ CO₂C₂H₅ — 4.179 Q₁₁ — t-C₄H₉ CO₂C₂H₅ — 4.180 Q₁₃ H — — H 4.181 Q₁₃ CH₃ — — CH₃ 4.182 Q₁₃ C₆H₅ — — CH₃ 4.183 Q₁₃ H — — CH₃ 4.184 Q₁₃ H — — 2-Thienyl 4.185 Q₁₃ CH₃ — — CON(CH₃)₂ 4.186 Q₁₃ CH₃ — — CH₂OC₂H₅ 4.187 Q₁₃ H — — CH(OC₂H₅)₂ 4.188 Q₁₃ H — —

4.189 Q₁₃

— — CH₃ 4.190 Q₁₃ C₆H₅ — — 2-Furyl 4.191 Q₁₃

— — 4-Cl-C₆H₄ 4.192 Q₁₃ C₆H₅ — — 2,4-Dichlorophenyl 4.193 Q₁₃ CH₃ — —

4.194 Q₁₃ (CH₂)₅Cl — — CH₂OCH₃ 4.195 Q₁₃ N(CH₃)C₈H₅ — — t-C₄H₉ 4.196 Q₁₃

— — CH₃ 4.197 Q₁₃ CH₃ — —

4.198 Q₁₃ CH₃ — — CF₃ 4.199 Q₁₆ OC₂H₅ — CH₃ — 4.200 Q₁₆ OH — i-C₃H₇ — 4.201 Q₁₆ OCH₃ — t-C₄H₉ — 4.202 Q₁₇ — H H — 4.203 Q₁₇ — H CH₃ — 4.204 Q₁₇ — H C₆H₅ — 4.205 Q₁₇ — H CN — 4.206 Q₁₇ — —CH═CH—CH═CH— — 4.207 Q₁₇ — —CF═CH—CH═CH— — 4.208 Q₁₇ — —CH═CH—CH═CF— — 4.209 Q₁₇ — —CH═CH—CCl═CH— — 4.210 Q₁₇ — —CH═CH—CH═CH— — 4.211 Q₁₇ — Si(CH₃)₃ H — 4.212 Q₁₇ — CH₃ H — 4.213 Q₁₇ — C₆H₅ H — 4.214 Q₁₇ — Si(CH₃)₃ CH₂OCH₃ — 4.215 Q₁₈ CH₂C₆H₅ H — — 4.216 Q₁₈ —CH═CH—CH═CH— — — 4.217 Q₁₈ H H — — 4.218 Q₁₈ H CH₃ — — 4.219 Q₁₈ CON(C₂H₅)₂ H — — 4.220 Q₁₈ NHCOOC₂H₅ H — — 4.221 Q₁₈ NHCOC₆H₅ H — — 4.222 Q₁₈ C₆H₅ SCH₃ — — 4.223 Q₁₈

CH₃ — — 4.224 Q₁₈ 4-Tolyl SCH₃ — — 4.225 Q₁₈

H — — 4.226 Q₁₈ H O-n-C₄H₉ — — 4.227 Q₁₈ —CH₂—(CH₂)₃—CH₂— — — 4.228 Q₁₈ H O-i-C₃H₇ — — 4.229 Q₁₈ —CH₂—(CH₂)₄—CH₂— — — 4.230 Q₁₈ CH₃ 4-Tolyl — — 4.231 Q₁₈ H 2-Tolyl — — 4.232 Q₁₈ H CBr₃ — — 4.233 Q₁₈ 4-Cl—C₆H₄ H — — 4.234 Q₁₈ —CH═CH—S— — — 4.235 Q₁₈ CH(OC₂H₅)₂ CH₃ — — 4.236 Q₁₈ 4-Cl—C₆H₄ CON(CH₃)₂ — — 4.237 Q₁₈ —S—CH═CH— — — 4.238 Q₁₅ H 4-Cl-C₆H₄ — — 4.239 Q₂₀ — CH₃ — CH₃ 4.240 Q₂₀ — i-C₄H₉ — H 4.241 Q₂₀ — i-C₃H₇ — CH₃ 4.242 Q₂₀ — C₂H₅ — CH₃ 4.243 Q₂₀ — CH₃ — t-C₄H₉ 4.244 Q₂₀ — s-C₄H₉ — H 4.245 Q₂₀ — i-C₄H₉ — CH₃ 4.246 Q₂₀ — Si(CH₃)₃ — H 4.247 Q₂₀ — n-C₃H₇ — H 4.248 Q₂₀ — CH₃ — CH₃ 4.249 Q₂₀ — OC₂H₅ — H 4.250 Q₂₀ — CH₃ — CN 4.251 Q₂₀ — H — C₆H₅ 4.252 Q₂₀ — CH₃ —

4.253 Q₂₀ — CH₃ — 3-Pyridyl 4.254 Q₂₀ — C₆H₅ — CONHCH₃ 4.255 Q₂₀ — NHCOCH₃ — CF₃ 4.256 Q₂₁ H — — C₆H₅ 4.257 Q₂₁ CH₂OCH₃ — — C₆H₅ 4.258 Q₂₁ CH₃ — — 4-Cl—C₆H₄ 4.259 Q₃₀ — — C₆H₅ — 4.260 Q₃₀ — — n-C₄H₉ — 4.261 Q₃₃ C₆H₅ — — — 4.262 Q₃₃ t-C₄H₉ — — — 4.263 Q₃₃ i-C₃H₇ — — — 4.264 Q₃₃ C₂H₅ — — — 4.265 Q₃₃ CH₃ — — — 4.266 Q₃₃ OCH₃ — — — 4.267 Q₃₃ O-n-C₄H₉ — — — 4.268 Q₃₃ N(C₂H₅)₂ — — — 4.269 Q₃₃ SCH₃ — — — 4.270 Q₃₃ S-c-C₆H₁₁ — — — 4.271 Q₃₃

— — — 4.272 Q₃₃

— — — 4.273 Q₃₃

— — — 4.274 Q₃₉ — — — CH₃ 4.275 Q₃₉ — — — C₆H₅ 4.276 Q₃₉ — — — n-C4H₉ 4.277 Q₂₀ — Cl — H 4.278 Q₂₀ — O—CH_(2CF) ₃ — H 4.279 Q₂₀ — —CN — H 4.280 Q₂₀ —

— H 4.281 Q₂₀ —

— H 4.282 Q₂₀ —

— H 4.283 Q₂ CH₃

—

TABLE 5 Compounds of the formula VIa (VIa)

Comp. No. Q_(i) R₂₁ R₂₂ R₂₃ R₂₄ XR₄ 5.001 Q₁ H —CH═CH—CH═N— CH₃

5.002 Q₁ CH₃ —C(Cl)═CH—CH═N— COCH₃

5.003 Q₁ —S—CH═CH— H 4-CH₃—C₆H₄

5.004 Q₁ —CH═CH—S— H 4-CH₃—C₆H₄

5.005 Q₂ H CH₃ H —

5.006 Q₂ H H H —

5.007 Q₂ H H —CH═CHCH₃ —

5.008 Q₂ H —CH═CH—CH═CH— —

5.009 Q₂

H H —

5.010 Q₂ H H SCH₃ —

5.011 Q₂ H H COOCH₃ —

5.012 Q₂ H H —CH═CH₂ —

5.013 Q₂ H H S(O)CH₃ —

5.014 Q₂ H H Si(CH₃)₃ —

5.015 Q₂ H —C(Cl)═CH—C(Cl)═CH— —

5.016 Q₂ H H COCH₃ —

5.017 Q₂ H H OCH₃ —

5.018 Q₂ H H Cl —

5.019 Q₂ H —C(OCH₃)═CH—CH═CH— —

5.020 Q₂ CH₃

—

5.021 Q₂ H —C(CH₃)═CH—CH═CH— —

5.022 Q₂ H —CH═CH—CH═C(CH₃)— —

5.023 Q₂ H H —C≡CH —

5.024 Q₂ OH —CH═CH—CH═CH— —

5.025 Q₂ H —CH═CH—CH═CH— —

5.026 Q₂ CH₃ —CH═C(CH₃)—C(CH₃)═CH— —

5.027 Q₂ H H H —

5.028 Q₂ CH₃ H H —

5.029 Q₂ H H C₂H₅ —

5.030 Q₂ Cl H H —

5.031 Q₂ H H n-C₆H₁₃ —

5.032 Q₂ H H CH₃ —

5.033 Q₂ —CH₂—C(CH₃)═C(CH₃)—CH₂— H —

5.034 Q₂ H H Sn(n-C₄H₉)₃ —

5.035 Q₂ H CH₃ H —

5.036 Q₂ H H SO₂CH₃ —

5.037 Q₂ —CH═C(CH₃)—C(CH₃)═CH— H —

5.038 Q₂ H H C₂H₅ —

5.039 Q₂ H H H —

5.040 Q₂ H H t-C₄H₉ —

5.041 Q₂ H H n-C₄H₉ —

5.042 Q₂ H H I —

5.043 Q₂ H H SCH₃ —

5.044 Q₂ H H B(OH)₂ —

5.045 Q₂ H H OCH₃ —

5.046 Q₂ H —CH═CH—CH═CH— —

5.047 Q₂ H —CO—NH—CH═CH— —

5.048 Q₂ H CH₃ F —

5.049 Q₂ OCH₃ H H —

5.050 Q₃ H H — CH₃

5.051 Q₃ H H — CON(C₂H₅)₂

5.052 Q₃ H H — Cl

5.053 Q₃ H H — OCH₃

5.054 Q₃ H Si(CH₃)₃ — CON(C₂H₅)₂

5.055 Q₃ H H — CH₂OCH₃

5.056 Q₃ —CH═CH—CH═CH— — CON(C₂H₅)₂

5.057 Q₃ CONH-t-C₄H₉ CH₃ — CH₃

5.058 Q₂ H H

—

5.059 Q₃ —CH═CH—CH═CH— — CH₂N(CH₃)₂

5.060 Q₃ —CH═CH—CH═CH— —

5.061 Q₄ H H H —

5.062 Q₄ H —CH═CH—CH═CH— —

5.063 Q₄ H CH₃ F —

5.064 Q₄ OCH₃ H H —

5.065 Q₄ H —CH═CH—CH═CH— —

5.066 Q₄ H H t-C₄H₉ —

5.067 Q₄ H H n-C₄H₉ —

5.068 Q₄ H H H —

5.069 Q₄ H H CH₃ —

5.070 Q₄ CH₃ H H —

5.071 Q₄ H H C₂H₅ —

5.072 Q₄ Cl H H —

5.073 Q₄ H H n-C₆H₁₃ —

5.074 Q₄ H H Si(CH₃)₃ —

5.075 Q₄ H H Sn(n-C₄H₉)₃ —

5.076 Q₄ H H H —

5.077 Q₄ H H t-C₄H₉ —

5.078 Q₄ H H I —

5.079 Q₄ H H B(OH)₂ —

5.080 Q₄ H H 2-thienyl —

5.081 Q₄ H CH₃ H —

5.082 Q₄ CH₃ H H —

5.083 Q₄ —CH₂—CH₂—CH₂—C(OCH₃)₂— SCH₃ —

5.084 Q₄ H H C₂H₅ —

5.085 Q₄ H

—

5.086 Q₄ H H COCH₃ —

5.087 Q₄

SCH₃ —

5.088 Q₄ H H CH₃ —

5.089 Q₄ H

—

5.090 Q₄ H —CH═CH—CH═CH— —

5.091 Q₄ CH₃ —C(CH₃)═C(SCH₃)—S— — SC₆H₅ 5.092 Q₄ H

—

5.093 Q₄ H H COOCH₃ —

5.094 Q₄ H H 2-thienyl —

5.095 Q₄ CH₃

—

5.096 Q₄ H —S—CH═CH— —

5.097 Q₄ H —CH═CH—CH═CH— —

5.098 Q₄ H H —C≡CH —

5.099 Q₄ CH₃ —CH═N—CH═N— —

5.100 Q₄ CH₃ —N═CH—N═CH— —

5.101 Q₄ CH₃

—

5.102 Q₄ H H —CH═CH₂ —

5.103 Q₄ H H Si(CH₃)₃ —

5.104 Q₄ H

—

5.105 Q₄ H H C₂H₅ —

5.106 Q₄ H

—

5.107 Q₄ H H —CH═CHCH₃ —

5.108 Q₄ H

—

5.109 Q₄ C₆H₅

—

5.110 Q₄ H H CH₃ —

5.111 Q₄ —CH₂—C(CH₃)₂—CH═C(OCH₃)— SCH₃ — OCH₂CF₃ 5.112 Q₄ CH₃ —C(CH₃)═CH—S— —

5.113 Q₄ H H n-C₆H₁₃ —

5.114 Q₄ CH₃

—

5.115 Q₄ H H SO₂CH₃ —

5.116 Q₄ CH₃

—

5.117 Q₄ Si(CH₃)₃ H H —

5.118 Q₄ CH₃

—

5.119 Q₄ H

—

5.120 Q₄ H H n-C₆H₁₃ —

5.121 Q₄ CH₃

—

5.122 Q₄ H

—

5.123 Q₄ CH₃

—

5.124 Q₄ CH₃

—

5.125 Q₄ H

—

5.126 Q₄ H CH₃ H —

5.127 Q₄ H

— OC₆H₅ 5.128 Q₄ H

—

5.129 Q₄ H

—

5.130 Q₄ H H I —

5.131 Q₄ H

—

5.132 Q₄ H H S(O)CH₃ —

5.133 Q₄ H —CH═CH—CH═C(CH₃)— —

5.134 Q₄ —(CH₂)₂NH₂ —CH═CH—C(OCH₃)═CH— —

5.135 Q₄ —(CH₂)₂N(CH₃)₂ —C(OCH₃)═CH—CH═CH— —

5.136 Q₄ H H B(OH)₂ —

5.137 Q₄ —(CH₂)₂OH —CH═CH—CH═CH— —

5.138 Q₄ —CH₂SH —CH═CH—CH═CH— —

5.139 Q₄ CH₃ —CH═CF—CH═CH— — OCH₂CF₃ 5.140 Q₄ H

— SCH₂C₆H₅ 5.141 Q₄ H H 2-thienyl —

5.142 Q₄ OCH₃

— OC₆H₅ 5.143 Q₄ H H SCH₃ —

5.144 Q₄ (CH₂)₂OCOCH₃

— OCH₂C₇F₁₅ 5.145 Q₄ H H Sn(CH₃)₃ —

5.146 Q₄ CH₂CON(CH₃)₂ —CH═CH—C(OCH₃)═CH— —

5.147 Q₄ H CH₃ H —

5.148 Q₄

—CH═CH—CH═CH— —

5.149 Q₄ H H OCH₃ —

5.150 Q₄ H —C(OH)═CH—CH═CH— —

5.151 Q₄ H H Sn(n-C₄H₉)₃ —

5.152 Q₄ CH₃ —CH═CH—CH═CH— —

5.153 Q₄ CH₂CO₂H —CH═CH—CH═CH— —

5.154 Q₄ CH₂CO₂C₂H₅ —CH═C(Cl)—CH═CH— —

5.155 Q₄ CH₃ —CH═C(Cl)—CH═CH— —

5.156 Q₄ H —CH═C(CH₃)—CH═CH— —

5.157 Q₄ H H Cl —

5.158 Q₄ CH₃ —CH═C(CH₃)—CH═CH— —

5.159 Q₄ H Si(CH₃)₃ H —

5.160 Q₄ NHC₄H₉ —CH═CH—CH═CH— —

5.161 Q₄ CH₂N(CH₃)₂ —CH═CH—CH═CH— —

5.162 Q₄

—CH═CH—CH═CH— —

5.163 Q₄ H H n-C₄H₉ —

5.164 Q₅ H H — C₆H₅

5.165 Q₅ H CH₃ — C₆H₅

5.166 Q₅ H CH₃ — CH₂OCH₃

5.167 Q₅ C₆H₅ CH₃ — CON(CH₃)₂

5.168 Q₅ —CH═CH—CH═CH— — CH₃

5.169 Q₅ H C₂H₅ — 2-Cl—C₆H₄

5.170 Q₅ H 3-(NH₂)—C₆H₄ — CH₃

5.171 Q₅ H C(OCH₃)₃ — i-C₃H₇

5.172 Q₅ H CH₃ — t-C₄H₉

5.173 Q₅ H SCH₃ — t-C₄H₉

5.174 Q₅ H 2-Thiazolyl — CH₃

5.175 Q₅

— CH₃

5.176 Q₅ H 3-Cl—C₆H₄ — CH₂OC₂H₅

5.177 Q₅ H CF₃ — CH₃

5.178 Q₅ H CH₃ — C₆H₅

5.179 Q₇ H — C₆H₅ H

5.180 Q₇ C₆H₅ — CH₃ H

5.181 Q₇ H — CH₃ C₆H₅

5.182 Q₇ CH₃ —

CH₃

5.183 Q₇ H — CH₃ OCH₃

5.184 Q₇ OCH₃ — CH₃ H

5.185 Q₇ N(CH₃)₂ — t-C₄H₉ CH₃

5.186 Q₇ CH₃ — t-C₄H₉ N(CH₃)₂

5.187 Q₈ — H H CH₂C₆H₅

5.188 Q₈ — H H SO₂C₆H₅

5.189 Q₈ — H H COO-t-C₄H₉

5.190 Q₈ — H H CONHt-C₄H₉

5.191 Q₈ — H H C₆H₅

5.192 Q₈ — H H CH₃

5.193 Q₈ — —CH═CH—CH═CH— n-C₃H₇

5.194 Q₈ — Cl Cl CH₂C₆H₅

5.195 Q₈ — H H CONHCH₃

5.196 Q₈ — —CH═CH—CH═CH— CO-t-C₄H₉

5.197 Q₈ — —CH═CH—CH═CH— CONHt-C₄H₉

5.198 Q₈ — CH₃ CH₃ CH₂OCH₃

5.199 Q₈ — —CH₂—CH₂—CH₂—CH₂— CON(CH₃)₂

5.200 Q₈ — H H SO₂NH₂

5.201 Q₁₁ — —CH═C(CH₃)—CH═CH— —

5.202 Q₁₁ — —CH═CH—C(CH₃)═CH— —

5.203 Q₁₁ — —CH═CH—C(Cl)═CH— —

5.204 Q₁₁ — —CH═CH—CH═CH— —

5.205 Q₁₁ — 3-NH₂—C₆H₄ H —

5.206 Q₁₁ — C₆H₅ H —

5.207 Q₁₁ — 2-Cl—C₆H₄ H —

5.208 Q₁₁ — 4-F—C₆H₄ H —

5.209 Q₁₁ — 2-Furyl H —

5.210 Q₁₁ — 4-Tolyl H —

5.211 Q₁₁ — 4-Anisyl H —

5.212 Q₁₁ — 2-Thienyl H —

5.213 Q₁₁ —

H —

5.214 Q₁₁ — 4-CF₃—C₆H₄ CO₂C₂H₅ — OC₈H₁₇ 5.215 Q₁₁ — C₆H₅ CO₂C₂H₅ —

5.216 Q₁₁ — 2,4-Dichlorophenyl CO₂C₂H₅ —

5.217 Q₁₁ — 3-Cl—C₆H₄ CO₂C₂H₅ —

5.218 Q₁₁ — t-C₄H₉ CO₂C₂H₅ —

5.219 Q₁₃ H — — H

5.220 Q₁₃ NHCOOt-C₄H₉ — — CH₃

5.221 Q₁₃ CH₃ — — CH₃

5.222 Q₁₃ C₆H₅ — — CH₃

5.223 Q₁₃ H — — CH₃

5.224 Q₁₃ H — — 2-Thienyl

5.225 Q₁₃ CH₃ — — CON(CH₃)₂

5.226 Q₁₃ CH₃ — — CH₂OC₂H₅

5.227 Q₁₃ H — — CH(OC₂H₅)₂

5.228 Q₁₃ H — —

5.229 Q₁₃

— — CH₃

5.230 Q₁₃ C₆H₅ — — 2-Furyl

5.231 Q₁₃

— — 4-Cl—C₆H₄

5.232 Q₁₃ C₆H₅ — — 2,4-Dichlorophenyl

5.233 Q₁₃ CH₃ — —

5.234 Q₁₃ (CH₂)₅Cl — — CH₂OCH₃

5.235 Q₁₃ N(CH₃)C₆H₅ — — t-C₄H₉ OCH(CF₃)₂ 5.236 Q₁₃

— — CH₃

5.237 Q₁₃ CH₃ — —

5.238 Q₁₃ CH₃ — — CF₃ OCH₂C₇F₁₅ 5.239 Q₁₆ OC₂H₅ — CH₃ —

5.240 Q₁₆ OH — i-C₃H₇ —

5.241 Q₁₆ OCH₃ — t-C₄H₉ —

5.242 Q₁₇ — H H — S-i-C₃H₇ 5.243 Q₁₇ — H CH₃ — OCH(CF₃)₂ 5.244 Q₁₇ — H C₆H₅ — OCH₂C₆F₅ 5.245 Q₁₇ — H CN — OC₆H₅ 5.246 Q₁₇ — —CH═CH—CH═CH— —

5.247 Q₁₇ — —CF═CH—CH═CH— —

5.248 Q₁₇ — —CH═CH—CH═CF— —

5.249 Q₁₇ — —CH═CH—CCl═CH— —

5.250 Q₁₇ — —CH═CH—CH═CH— —

5.251 Q₁₇ — Si(CH₃)₃ H — OCH₂C₃F₇ 5.252 Q₁₇ — CH₃ H —

5.253 Q₁₇ — C₆H₅ H —

5.254 Q₁₇ — Si(CH₃)₃ CH₂OCH₃ —

5.255 Q₁₈ CH₂C₆H₅ H — —

5.256 Q₁₈ H NHCOO-t-C₄H₉ — —

5.257 Q₁₈ C₆H₅ NHCO-t-C₄H₉ — —

5.258 Q₁₈ C₆H₅ CONHN(CH₃)₂ — —

5.259 Q₁₈ —CH═CH—CH═CH— — —

5.260 Q₁₈ H H — —

5.261 Q₁₈ H CH₃ — —

5.262 Q₁₈ NH₂ H — —

5.263 Q₁₈ NH₂ CH₃ — —

5.264 Q₁₈ CON(C₂H₅)₂ H — —

5.265 Q₁₈ NHCOOC₂H₅ H — —

5.266 Q₁₈ NHCOC₆H₅ H — —

5.267 Q₁₈ C₆H₅ SCH₃ — —

5.268 Q₁₈

CH₃ — —

5.269 Q₁₈ 4-Tolyl SCH₃ — —

5.270 Q₁₈

H — —

5.271 Q₁₈ H O-n-C₄H₉ — —

5.272 Q₁₈ —CH₂—(CH₂)₃—CH₂— — —

5.273 Q₁₈ H O-i-C₃H₇ — —

5.274 Q₁₈ —CH₂—(CH₂)₄—CH₂— — —

5.275 Q₁₈ CH₃ 4-Tolyl — —

5.276 Q₁₈ H 2-Tolyl — —

5.277 Q₁₈ H CBr₃ — — OCH₂CH(CF₃)₂ 5.278 Q₁₈ 4-Cl—C₆H₄ H — —

5.279 Q₁₈ —CH═CH—S— — —

5.280 Q₁₈ CH(OC₂H₅)₂ CH₃ — —

5.281 Q₁₈ 4-Cl—C₆H₄ CON(CH₃)₂ — —

5.282 Q₁₈ —S—CH═CH— — —

5.283 Q₁₈ H 4-Cl—C₆H₄ — —

5.284 Q₂₀ — CH₃ — CH₃

5.285 Q₂₀ — NHCOO-t-C₄H₉ — H

5.286 Q₂₀ — NHCOO-t-C₄H₉ — CH₃

5.287 Q₂₀ — i-C₄H₉ — H

5.288 Q₂₀ — i-C₃H₇ — CH₃

5.289 Q₂₀ — C₂H₅ — CH₃

5.290 Q₂₀ — NH₂ —

5.291 Q₂₀ — NH₂ — 4-Cl—C₆H₄

5.292 Q₂₀ — CH₃ — t-C₄H₉

5.293 Q₂₀ — s-C₄H₉ — H

5.294 Q₂₀ — i-C₄H₉ — CH₃ O-i-C₃H₇ 5.295 Q₂₀ — Si(CH₃)₃ — H

5.296 Q₂₀ — n-C₃H₇ — H O-c-C₆H₁₁ 5.297 Q₂₀ — CH₃ — CH₃

5.298 Q₂₀ — OC₂H₅ — H

5.299 Q₂₀ — CH₃ — CN

5.300 Q₂₀ — H — C₆H₅

5.301 Q₂₀ — CH₃ —

5.302 Q₂₀ — CH₃ — 3-Pyridyl

5.303 Q₂₀ — C₆H₅ — CONHCH₃

5.304 Q₂₀ — NHCOCH₃ — CF₃

5.305 Q₂₁ H — — C₆H₅

5.306 Q₂₁ CH₂OCH₃ — — C₆H₅

5.307 Q₂₁ CH₃ — — 4-Cl—C₆H₄

5.308 Q₃₀ — — C₆H₅ —

5.309 Q₃₀ — — n-C₄H₉ —

5.310 Q₃₃ C₆H₅ — — —

5.311 Q₃₃ t-C₄H₉ — — —

5.312 Q₃₃ i-C₃H₇ — — —

5.313 Q₃₃ C₂H₅ — — —

5.314 Q₃₃ CH₃ — — —

5.315 Q₃₃ OCH₃ — — —

5.316 Q₃₃ O-n-C₄H₉ — — —

5.317 Q₃₃ N(C₂H₅)₂ — — —

5.318 Q₃₃ SCH₃ — — —

5.319 Q₃₃ S-c-C₆H₁₁ — — —

5.320 Q₃₃

— — — OC₈H₁₇ 5.321 Q₃₃

— — —

5.322 Q₃₃

— — —

5.323 Q₃₉ — — — CH₃

5.324 Q₃₉ — — — C₆H₅

5.325 Q₃₉ — — — n-C₄H₉

5.326 Q₂₀ — Cl — H

5.327 Q₂₀ — O—CH₂CF₃ — H

5.328 Q₂₀ — —CN — H

5.329 Q₂₀ —

— H

5.330 Q₂₀ —

— H

5.331 Q₂₀ —

— H

5.332 Q₂₀ — Cl — H OCH₂CF₃ 5.333 Q₂₀ — OCH₂CF₃ — H OCH₂CF₃ 5.334 Q₂₀ — Cl — H

TABLE 6 Compounds of the formula Vllla

Comp. No. Q₁ R₂₁ R₂₂ R₂₃ R₂₄ 6.001 Q₁ H —CH═CH—CH═N— CH₃ 6.002 Q₁ CH₃ —C(Cl)═CH—CH═N— COCH₃ 6.003 Q₁ —S—CH═CH— H 4-CH₃—C₆H₄ 6.004 Q₁ —CH═CH—S— H 4-CH₃—C₆H₄ 6.005 Q₂ H CH₃ H — 6.006 Q₂ H H H — 6.007 Q₂ H H —CH═CHCH₃ 6.008 Q₂ H —CH═CH—CH═CH— — 6.009 Q₂

H H — 6.010 Q₂ H H SCH₃ — 6.011 Q₂ H H COOCH₃ — 6.012 Q₂ H H —CH═CH₂ — 6.013 Q₂ H H S(O)CH₃ — 6.014 Q₂ H H Si(CH₃)₃ — 6.015 Q₂ H —C(Cl)═CH—C(Cl)═CH— — 6.016 Q₂ H H COCH₃ — 6.017 Q₂ H H OCH₃ — 6.018 Q₂ H H Cl — 6.019 Q₂ H —C(OCH₃)═CH— — CH═CH— 6.020 Q₂ CH₃

— 6.021 Q₂ H —C(CH₃)═CH—CH═CH— — 6.022 Q₂ H —CH═CH—CH═C(CH₃)— — 6.023 Q₂ H H —C≡CH — 6.024 Q₂ OH —CH═CH—CH═CH— — 6.025 Q₂ CH₃ —CH═C(CH₃)—C(CH₃)═CH— — 6.026 Q₂ CH₃ H H — 6.027 Q₂ H H C₂H₅ 6.028 Q₂ Cl H H — 6.029 Q₂ H H n-C₆H₁₃ — 6.030 Q₂ H H CH₃ — 6.031 Q₂ —CH₂—C(CH₃)═C(CH₃)—CH₂— H — 6.032 Q₂ H H Sn(n-C₄H₉)₃ — 6.033 Q₂ H H SO₂CH₃ — 6.034 Q₂ H H t-C₄H₉ — 6.035 Q₂ H H n-C₄H₉ — 6.036 Q₂ H H I — 6.037 Q₂ H H B(OH)₂ — 6.038 Q₂ H —CO—NH—CH═CH— — 6.039 Q₂ H CH₃ F — 6.040 Q₂ OCH₃ H H — 6.041 Q₃ H H — CH₃ 6.042 Q₃ H H — CON(C₂H₅)₂ 6.043 Q₃ H H — Cl 6.044 Q₃ H H — OCH₃ 6.045 Q₃ H Si(CH₃)₃ — CON(C₂H₅)₂ 6.046 Q₃ H H — CH₂OCH₃ 6.047 Q₃ —CH═CH—CH═CH— — CON(C₂H₅)₂ 6.048 Q₃ CONH-t- CH₃ — CH₃ C₄H₉ 6.049 Q₂ H H

— 6.050 Q₃ —CH═CH—CH═CH— — CH₂N(CH₃)₂ 6.051 Q₃ —CH═CH—CH═CH— —

6.052 Q₄ H H H — 6.053 Q₄ H —CH═CH—CH═CH— — 6.054 Q₄ H CH₃ F — 6.055 Q₄ OCH₃ H H — 6.056 Q₄ H H t-C₄H₉ — 6.057 Q₄ H H n-C₄H₉ — 6.058 Q₄ H H CH₃ — 6.059 Q₄ CH₃ H H — 6.060 Q₄ H H C₂H₅ — 6.061 Q₄ Cl H H — 6.062 Q₄ H H n-C₆H₁₃ — 6.063 Q₄ H H Si(CH₃)₃ — 6.064 Q₄ H H Sn(n-C₄H₉)₃ — 6.065 Q₄ H H I — 6.066 Q₄ H H B(OH)₂ — 6.067 Q₄ H H 2-thienyl — 6.068 Q₄ H CH₃ H — 6.069 Q₄ —CH₂—CH₂—CH₂— SCH₃ — C(OCH₃)₂— 6.070 Q₄ H

— 6.071 Q₄ H H COCH₃ — 6.072 Q₄

SCH₃ — 6.073 Q₄ H

— 6.074 Q₄ CH₃ —C(CH₃)═C(SCH₃)—S— — 6.075 Q₄ H

— 6.076 Q₄ H H COOCH₃ — 6.077 Q₄ CH₃

— 6.078 Q₄ H —S—CH═CH— — 6.079 Q₄ H H —C≡CH — 6.080 Q₄ CH₃ —CH═N—CH═N— — 6.081 Q₄ CH₃ —N═CH—N═CH— — 6.082 Q₄ CH₃

— 6.083 Q₄ H H —CH═CH₂ — 6.084 Q₄ H

— 6.085 Q₄ H

— 6.086 Q₄ H H —CH═CHCH₃ — 6.087 Q₄ H

— 6.088 Q₄ C₆H₅

— 6.089 Q₄ —CH₂—C(CH₃)₂—CH═C(OCH₃)— SCH₃ — 6.090 Q₄ CH₃ —C(CH₃)═CH—S— — 6.091 Q₄ CH₃

— 6.092 Q₄ H H SO₂CH₃ — 6.093 Q₄ CH₃

— 6.094 Q₄ Si(CH₃)₃ H H — 6.095 Q₄ CH₃

— 6.096 Q₄ CH₃

— 6.097 Q₄ H

— 6.098 Q₄ CH₃

— 6.099 Q₄ CH₃

— 6.100 Q₄ H

— 6.101 Q₄ H

— 6.102 Q₄ H

— 6.103 Q₄ H

— 6.104 Q₄ H

— 6.105 Q₄ H H S(O)CH₃ — 6.106 Q₄ H —CH═CH—CH═C(CH₃)— — 6.107 Q₄ —(CH₂)₂NH₂ —CH═CH— — C(OCH₃)═CH— 6.108 Q₄ —(CH₂)₂N(CH₃)₂ —C(OCH₃)═CH— — CH═CH— 6.109 Q₄ —(CH₂)₂OH —CH═CH—CH═CH— — 6.110 Q₄ —CH₂SH —CH═CH—CH═CH— — 6.111 Q₄ CH₃ —CH═CF—CH═CH— — 6.112 Q₄ H

— 6.113 Q₄ OCH₃

— 6.114 Q₄ H H SCH₃ — 6.115 Q₄ H H Sn(CH₃)₃ — 6.116 Q₄ CH₂CON(CH₃)₂ —CH═CH— — C(OCH₃)═CH— 6.117 Q₄ H CH₃ H — 6.118 Q₄ H H OCH₃ — 6.119 Q₄ H —C(OH)═CH—CH═CH— — 6.120 Q₄ CH₃ —CH═CH—CH═CH— — 6.121 Q₄ CH₂CO₂H —CH═CH—CH═CH— — 6.122 Q₄ CH₂CO₂C₂H₅ —CH═C(Cl)—CH═CH— — 6.123 Q₄ CH₃ —CH═C(Cl)—CH═CH— — 6.124 Q₄ H —CH═C(CH₃)—CH═CH— — 6.125 Q₄ H H Cl — 6.126 Q₄ CH₃ —CH═C(CH₃)—CH═CH— — 6.127 Q₄ H Si(CH₃)₃ H — 6.128 Q₄ CH₂N(CH₃)₂ —CH═CH—CH═CH— — 6.129 Q₄

—CH═CH—CH═CH— — 6.130 Q₅ H H — C₆H₅ 6.131 Q₅ H CH₃ — C₆H₅ 6.132 Q₅ H CH₃ — CH₂OCH₃ 6.133 Q₅ C₆H₅ CH₃ — CON(CH₃)₂ 6.134 Q₅ —CH═CH—CH═CH— — CH₃ 6.135 Q₅ H C₂H₅ — 2-Cl—C₆H₄ 6.136 Q₅ H C(OCH₃)₃ — i-C₃H₇ 6.137 Q₅ H CH₃ — t-C₄H₉ 6.138 Q₅ H SCH₃ — t-C₄H₉ 6.139 Q₅ H 2- — CH₃ Thiazolyl 6.140 Q₅

— CH₃ 6.141 Q₅ H 3-Cl—C₆H₄ — CH₂OC₂H₅ 6.142 Q₅ H CF₃ — CH₃ 6.143 Q₇ H — C₆H₅ H 6.144 Q₇ C₆H₅ — CH₃ H 6.145 Q₇ H — CH₃ C₆H₅ 6.146 Q₇ CH₃ —

CH₃ 6.147 Q₇ H — CH₃ OCH₃ 6.148 Q₇ OCH₃ — CH₃ H 6.149 Q₇ N(CH₃)₂ — t-C₄H₉ CH₃ 6.150 Q₇ CH₃ — t-C₄H₉ N(CH₃)₂ 6.151 Q₈ — H H CH₂C₆H₅ 6.152 Q₈ — H H SO₂C₆H₅ 6.153 Q₈ — H H C₆H₅ 6.154 Q₈ — H H CH₃ 6.155 Q₈ — —CH═CH—CH═CH— n-C₃H₇ 6.156 Q₈ — Cl Cl CH₂C₆H₅ 6.157 Q₈ — H H CONHCH₃ 6.158 Q₈ — —CH═CH—CH═CH— CO-t-C₄H₉ 6.159 Q₈ — —CH═CH—CH═CH— CONHt-C₄H₉ 6.160 Q₈ — CH₃ CH₃ CH₂OCH₃ 6.161 Q₈ — —CH₂—CH₂—CH₂—CH₂— CON(CH₃)₂ 6.162 Q₈ — H H SO₂(CH3)₂ 6.163 Q₁₁ — —CH═C(CH₃)—CH═CH— — 6.164 Q₁₁ — —CH═CH—C(CH₃)═CH— — 6.165 Q₁₁ — —CH═CH—C(Cl)═CH— — 6.166 Q₁₁ — —CH═CH—CH═CH— — 6.167 Q₁₁ — C₆H₅ H — 6.168 Q₁₁ — 2-Cl—C₆H₄ H — 6.169 Q₁₁ — 4-F—C₆H₄ H — 6.170 Q₁₁ — 2-Furyl H — 6.171 Q₁₁ — 4-Tolyl H — 6.172 Q₁₁ — 4-Anisyl H — 6.173 Q₁₁ — 2-Thienyl H — 6.174 Q₁₁ —

H — 6.175 Q₁₁ — 4-CF₃— CO₂C₂H₅ — C₆H₄ 6.176 Q₁₁ — C₆H₅ CO₂C₂H₅ — 6.177 Q₁₁ — 2,4- CO₂C₂H₅ — Dichloro- phenyl 6.178 Q₁₁ — 3-Cl—C₆H₄ CO₂C₂H₅ — 6.179 Q₁₁ — t-C₄H₉ CO₂C₂H₅ — 6.180 Q₁₃ H — — H 6.181 Q₁₃ CH₃ — — CH₃ 6.182 Q₁₃ C₆H₅ — — CH₃ 6.183 Q₁₃ H — — CH₃ 6.184 Q₁₃ H — — 2-Thienyl 6.185 Q₁₃ CH₃ — — CON(CH₃)₂ 6.186 Q₁₃ CH₃ — — CH₂OC₂H₅ 6.187 Q₁₃ H — — CH(OC₂H₅)₂ 6.188 Q₁₃ H — —

6.189 Q₁₃

— — CH₃ 6.190 Q₁₃ C₆H₅ — — 2-Furyl 6.191 Q₁₃

— — 4-Cl—C₆H₄ 6.192 Q₁₃ C₆H₅ — — 2,4-Dichloro- phenyl 6.193 Q₁₃ CH₃ — —

6.194 Q₁₃ (CH₂)₅Cl — — CH₂OCH₃ 6.195 Q₁₃ N(CH₃)C₆H₅ — — t-C₄H₉ 6.196 Q₁₃

— — CH₃ 6.197 Q₁₃ CH₃ — —

6.198 Q₁₃ CH₃ — — CF₃ 6.199 Q₁₆ OC₂H₅ — CH₃ — 6.200 Q₁₆ OH — i-C₃H₇ — 6.201 Q₁₆ OCH₃ — t-C₄H₉ — 6.202 Q₁₇ — H H — 6.203 Q₁₇ — H CH₃ — 6.204 Q₁₇ — H C₆H₅ — 6.205 Q₁₇ — H CN — 6.206 Q₁₇ — —CH═CH—CH═CH— — 6.207 Q₁₇ — —CF═CH—CH═CH— — 6.208 Q₁₇ — —CH═CH—CH═CF— — 6.209 Q₁₇ — —CH═CH—CCl═CH— — 6.210 Q₁₇ — —CH═CH—CH═CH— — 6.211 Q₁₇ — Si(CH₃)₃ H — 6.212 Q₁₇ — CH₃ H — 6.213 Q₁₇ — C₆H₅ H — 6.214 Q₁₇ — Si(CH₃)₃ CH₂OCH₃ — 6.215 Q₁₈ CH₂C₆H₅ H — — 6.216 Q₁₈ —CH═CH—CH═CH— — — 6.217 Q₁₈ H H — — 6.218 Q₁₈ H CH₃ — — 6.219 Q₁₈ CON(C₂H₅)₂ H — — 6.220 Q₁₈ NHCOOC₂H₅ H — — 6.221 Q₁₈ NHCOC₆H₅ H — — 6.222 Q₁₈ C₆H₅ SCH₃ — — 6.223 Q₁₈

CH₃ — — 6.224 Q₁₈ 4-Tolyl SCH₃ — — 6.225 Q₁₈

H — — 6.226 Q₁₈ H O-n-C₄H₉ — — 6.227 Q₁₈ —CH2—(CH₂)₃—CH₂— — — 6.228 Q₁₈ H O-i-C₃H₇ — — 6.229 Q₁₈ —CH₂—(CH₂)₄—CH₂— — — 6.230 Q₁₈ CH₃ 4-Tolyl — — 6.231 Q₁₈ H 2-Tolyl — — 6.232 Q₁₈ H CBr₃ — — 6.233 Q₁₈ 4-Cl—C₆H₄ H — — 6.234 Q₁₈ —CH═CH—S— — — 6.235 Q₁₈ CH(OC₂H₅)₂ CH₃ — — 6.236 Q₁₈ 4-Cl—C₆H₄ CON(CH₃)₂ — — 6.237 Q₁₈ —S—CH═CH— — — 6.238 Q₁₈ H 4-Cl—C₆H₄ — — 6.239 Q₂₀ — CH₃ — CH₃ 6.240 Q₂₀ — i-C₄H₉ — H 6.241 Q₂₀ — i-C₃H₇ — CH₃ 6.242 Q₂₀ — C₂H₅ — CH₃ 6.243 Q₂₀ — CH₃ — t-C₄H₉ 6.244 Q₂₀ — s-C₄H₉ — H 6.245 Q₂₀ — i-C₄H₉ — CH₃ 6.246 Q₂₀ — Si(CH₃)₃ — H 6.247 Q₂₀ — n-C₃H₇ — H 6.248 Q₂₀ — CH₃ — CH₃ 6.249 Q₂₀ — OC₂H₅ — H 6.250 Q₂₀ — CH₃ — CN 6.251 Q₂₀ — H — C₆H₅ 6.252 Q₂₀ — CH₃ —

6.253 Q₂₀ — CH₃ — 3-Pyridyl 6.254 Q₂₀ — C₆H₅ — CONHCH₃ 6.255 Q₂₀ — NHCOCH₃ — CF₃ 6.256 Q₂₁ H — — C₆H₅ 6.257 Q₂₁ CH₂OCH₃ — — C₆H₅ 6.258 Q₂₁ CH₃ — — 4-Cl—C₆H₄ 6.259 Q₃₀ — — C₆H₅ — 6.260 Q₃₀ — — n-C₄H₉ — 6.261 Q₃₃ C₆H₅ — — — 6.262 Q₃₃ t-C₄H₉ — — — 6.263 Q₃₃ i-C₃H₇ — — — 6.264 Q₃₃ C₂H₅ — — — 6.265 Q₃₃ CH₃ — — — 6.266 Q₃₃ OCH₃ — — — 6.267 Q₃₃ O-n-C₄H₉ — — — 6.268 Q₃₃ N(C₂H₅)₂ — — — 6.269 Q₃₃ SCH₃ — — — 6.270 Q₃₃ S-c-C₆H₁₁ — — — 6.271 Q₃₃

— — — 6.272 Q₃₃

— — — 6.273 Q₃₃

— — — 6.274 Q₃₉ — — — CH₃ 6.275 Q₃₉ — — — C₆H₅ 6.276 Q₃₉ — — — n-C₄H₉ 6.277 Q₂₀ — Cl — H 6.278 Q₂₀ — O—CH₂CF₃ — H 6.279 Q₂₀ — —CN — H 6.280 Q₂₀ —

— H 6.281 Q₂₀ —

— H 6.282 Q₂₀ —

— H 6.283 Q₂ CH₃

—

TABLE 7 Physical data of the compounds from Tables 2-6: Physical data Compound No. Melting point 2.006 195-196° C. 2.008 185° C. (decomposition) 2.009 195-196° C. 2.025 232° C. (decomposition) 2.027 202-203° C. (decomposition) 2.039 166-167° C. (decomposition) 2.046 230° C. (decomposition) 2.058 125-127° C. 2.061 179-180° C. 2.062 213° C. (decomposition) 2.066 144-147° C. 2.067 174-176° C. 2.068 203° C. (decomposition) 2.076 214-215° C. (decomposition) 2.077 192-200° C. (decomposition) 2.082 165-167° C. (decomposition) 2.084 208-209° C. 2.088 206-207° C. (decomposition) 2.090 250° C. (decomposition) 2.094 231° C. (decomposition) 2.097 258° C. (decomposition) 2.105 167-168° C. 2.110 162-163° C. 2.113 165-166° C. 2.120 146-147° C. 2.126 189-190° C. 2.141 230° C. (decomposition) 2.147 159-160° C. (decomposition) 2.149 210° C. (decomposition) 2.157 169-170° C. 2.163 170-173° C. 2.192 205-206° C. 2.250 211° C. (decomposition) 2.260 198-199° C. (decomposition) 2.297 188-189° C. (decomposition) 2.326 157-158° C. (decomposition) 2.327 193-194° C. 4.008 128° C. 4.009 not determined 4.049 not determined 4.052 100-103° C. (decomposition) 4.053 122-123° C. (decomposition) 4.056 124-129° C. (decomposition) 4.057 oil 4.058 86-87° C. 4.059 118-120° C. (decomposition) 4.060 61-62° C. 4.062 oil 4.067 118-119° C. (decomposition) 4.068 86° C. 4.118 105-106° C. (decomposition) 4.125 112-112° C. (decomposition) 4.206 211° C. (decomposition) 4.217 solid 6.006 215° C. (decomposition) 6.008 216° C. (decomposition) 6.009 158° C. (decomposition) 6.049 157° C. (decomposition) 6.052 217° C. (decomposition) 6.053 224° C. (decomposition) 6.056 167-168° C. (decomposition) 6.057 146-148° C. (decomposition) 6.058 222° C. (decomposition) 6.059 200° C. (decomposition) 6.060 172° C. (decomposition) 6.062 85° C. (decomposition) 6.067 235° C. (decomposition) 6.068 192° C. (decomposition) 6.118 185° C. (decomposition) 6.125 223° C. (decomposition) 6.206 232° C. (decomposition) 6.217 solid 6.239 181° C. (decomposition) 2.200 179-180° C. 2.337 223-224° C. 2.102 158-160° C. 2.332 205-207° C. 2.333 172-173° C. 2.328 159-160° C. 4.154 115° C. (decomposition) 4.162 >200° C. 4.083 crystalline 4.283 156° C. (decomposition) 4.277 112-120° C. (decomposition) 5.326 crystalline 6.154 164° C. 6.162 168-170° C. 6.083 crystalline 6.283 crystalline 6.278 211° C. (decomposition)

Formulation Examples for Active Substances of the Formula I

(%=per cent by weight)

F1. Emulsion concentrate a) b) c) d) Active substance according to  5% 10% 25% 50% Tables 2-3 Ca dodecylbenzenesulfonate  6%  8%  6%  8% Castor oil polyglycol ether  4% —  4%  4% (36 mol of EO) Octylphenol polyglycol ether —  4% —  2% (7-8 mol of EO) Cyclohexanone — — 10% 20% Aromatic hydrocarbon 85% 78% 55% 16% mixture C₉-C₁₂

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

F2. Solutions a) b) c) d) Active substance according  5% 10% 50% 90% to Tables 2-3 1-Methoxy-3-(3-methoxy- propoxy)-propane — 20% 20% — Polyethylene glycol MW 400 20% 10% — — N-Methyl-2-pyrrolidone — — 30% 10% Aromatic hydrocarbon 75% 60% — — mixture C₉-C₁₂

The solutions are suitable for use in the form of tiny drops.

F3. Wettable powders a) b) c) d) Active substance according  5% 25% 50% 80% to Tables 2-3 Sodium ligninsulfonate  4% —  3% — Sodium lauryl sulfate  2%  3% —  4% Sodium diisobutyl-naphthalene- —  6%  5%  6% sulfonate Octylphenol polyglycol ether —  1%  2% — (7-8 mol of EO) Highly disperse silicic acid  1%  3%  5% 10% Kaolin 88% 62% 35% —

The active substance is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders which can be diluted with water to give suspensions of any desired concentration are obtained.

F4. Coated granules a) b) c) Active substance according 0.1%  5% 15% to Tables 2-3 Highly disperse silicic acid 0.9%  2%  2% Inorganic carrier material 99.0% 93% 83% (Ø 0.1-1 mm) for exampie CaCO₃ or SiO₂

The active substance is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.

F5. Coated granules a) b) c) Active substance according 0.1%  5% 15% to Tables 2-3 Polyethylene glycol MW 200 1.0%  2%  3% Highly disperse silicic acid 0.9%  1%  2% Inorganic carrier material 98.0% 92% 80% (Ø 0.1-1 mm) for example CaCO₃ or SiO₂

The finely ground active substance is applied uniformly to the carrier material, which is moistened with polyethylene glycol, in a mixer. Dust-free coated granules are obtained in this manner.

F6. Extruded granules a) b) c) d) Active substance according 0.1%  3%  5%  15% to Tables 2-3 Sodium ligninsulfonate 1.5%  2%  3%  4% Carboxymethylcellulose 1.4%  2%  2%  2% Kaolin 97.0% 93% 90% 79%

The active substance is mixed with the additives and the mixture is ground and moistened with water. This mixture is extruded and then dried in a stream of air.

F7. Dusts a) b) c) Active substance according  0.1%  1%  5% to Tables 2-3 Talc 39.9% 49% 35% Kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active substance with the carriers and grinding the mixture on a suitable mill.

F8. Suspension Concentrates a) b) c) d) Active substance according  3% 10% 25% 50% to Tables 2-3 Ethylene glycol  5%  5%  5%  5% Nonylphenol polyglycol ether —  1%  2% (15 mol of EO) Sodium ligninsulfonate  3%  3%  4%  5% Carboxymethylcellulose  1%  1%  1%  1% 37% strength aqueous  0.2%  0.2%  0.2%  0.2% formaldehyde solution Silicone oil emulsion  0.8%  0.8%  0.8%  0.8% Water 87% 79% 62% 38%

The finely ground active substance is mixed intimately with the additives. A suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water is thus obtained.

Biological Examples EXAMPLE B1 Herbicidal Action Before the Emergence of the Plants (Pre-emergence Action)

Monocotyledon and dicotyledon test plants are sown in standard soil in plastic pots. Immediately after sowing, the test substances are sprayed on as an aqueous suspension (prepared from a 25% wettable powder (Example F3, b)) or as an emulsion (prepared from a 25% emulsion concentrate (Example F1, c)) in a dosage corresponding to 2 kg of AS/ha (500 l of water/ha). The test plants are then grown under optimum conditions in a greenhouse. After a test duration of 3 weeks, the test is evaluated by a nine-level scale of ratings (1=complete damage, 9=no action). Rating values of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action. In this test, the compounds of the formula I show a good herbicidal action. Examples of the herbicidal action of the compounds of the formula I are given in Table B1:

TABLE B1 Pre-emergence action of the compounds of the formula I: Compound No. Avena Setaria Sinapis Stellaria 2.025 2 1 1 1 2.039 2 1 1 1 2.061 2 1 1 1 2.066 3 1 1 1 2.082 2 1 1 1 2.088 3 2 1 1 2.090 4 2 1 1 2.105 3 2 1 i 2.110 2 1 1 1 2.147 2 1 i 1 2.297 1 1 1 1

EXAMPLE B2 Post-emergence Herbicidal Action

Monocotyledon and dicotyledon test plants are grown in plastic pots with standard soil in a greenhouse and, in the 4- to 6-leaf stage, are sprayed with an aqueous suspension of the test substances of the formula I, prepared from a 25% wettable powder (Example F3, b)) or with an emulsion of the test substances of the formula I, prepared from a 25% emulsion concentrate (Example F1, c)), in a dosage corresponding to 2 kg of AS/ha (500 l of water/ha). The test plants are then grown further under optimum conditions in a greenhouse. After a test duration of about 18 days, the test is evaluated with a nine-level scale of ratings (1=complete damage, 9=no action). Rating values of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action. In this test also, the compounds of the formula I show a potent herbicidal action. Examples of the herbicidal action of the compounds of the formula I are given in Table B2:

TABLE B2 Post-emergence action of the compounds of the formula I: Compound No. Avena Setaria Sinapis Stellaria 2.025 1 4 2 3 2.039 2 4 2 4 2.061 1 4 2 2 2.066 1 6 1 3 2.082 2 4 3 2 2.088 2 5 2 3 2.090 1 6 1 2 2.105 1 3 1 2 2.110 1 2 2 1 2.147 1 3 1 2 2.297 1 2 1 2 

What is claimed is:
 1. A compound of the formula I

in which Q_(i) is the group

X is oxygen; R₂ and R₃ are hydrogen; R₄ is phenyl substituted by nitro, C₁-C₁₀-halogenalkyl, COOH, —CH₂—CH₂—COOH, C₁-C₁₀-alkoxy or halogen; R₂₁, R₂₂, R₂₃ and R₂₄ independently of one another are hydrogen,

 2-thienyl, C₂-C₈-alkenyl, halogen, SO₂N(CH₃)₂ or C₁-C₁₀-alkyl, which C₁-C₁₀-alkyl in turn can be substituted by OR₅, wherein R₅ is C₁-C₆-alkyl, or R₂₂ and R₂₃ together are —CH═CH—CH═CH—, or an agronomically tolerated salt/N-oxide/isomer/enantiomer of this compound.
 2. A composition for use as a herbicide or plant growth inhibitor which comprises a herbicidally effective or plant growth inhibiting effective amount of a compound of the formula I according to claim 1 and an inert carrier.
 3. The composition according to claim 2, which comprises between 0.1% and 95% of the compound of the formula I.
 4. A method of controlling unwanted plant growth, which comprises applying an effective controlling amount of the compound of the formula I according to claim 1 or a composition comprising this compound to the plants, plant parts, seeds or their environment.
 5. A method according to claim 4, wherein the compound is applied in an amount of between 0.001 and 4 kg per hectare.
 6. A method of inhibiting plant growth, which comprises applying the compound of the formula I according to claim 1 or a composition comprising this compound to the plants, plant parts, seeds or their environment in a herbicidally effective amount. 